公开(公告)号：US08101780B2

公开(公告)日：2012-01-24

申请号：US12668242

申请日：2008-07-07

申请人： Heidi Emilia Saxell ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Cedric Dieleman

发明人： Heidi Emilia Saxell ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Cedric Dieleman

IPC分类号： C07D231/10

CPC分类号： C07D231/14

摘要： The present invention relates to a new crystalline form of 3-(Difluormethyl)-1-methyl-N-(3′,4′,5′-trifluor[1,1′-biphenyl]-2-yl)-1H-pyrazol-4-carboxamide. The invention also relates to processes for the production of this crystalline form and formulations for plant protection which contain the crystalline form of 3-(Difluormethyl)-1-methyl-N-(3′,4′,5′-trifluor[1,1′-biphenyl]-2-yl)-1H-pyrazol-4-carboxamide.

摘要翻译： 本发明涉及3-（二甲基甲基）-1-甲基-N-（3'，4'，5'-三氟[1,1'-联苯] -2-基）-1H-吡唑的新结晶形式 -4-甲酰胺。 本发明还涉及生产该结晶形式的方法和用于植物保护的制剂，其含有3-（二甲基甲基）-1-甲基-N-（3'，4'，5'-三氟[ 联苯] -2-基）-1H-吡唑-4-甲酰胺。

公开(公告)号：US20100255996A1

公开(公告)日：2010-10-07

申请号：US12668242

申请日：2008-07-07

申请人： Heidi Emilia Saxell ,  Jochen Dietz ,  Sebastian Peer SMIDT ,  Cedric Dieleman

发明人： Heidi Emilia Saxell ,  Jochen Dietz ,  Sebastian Peer SMIDT ,  Cedric Dieleman

IPC分类号： A01N43/56 ,  C07D231/14

CPC分类号： C07D231/14

摘要： The present invention relates to a new crystalline form of 3-(Difluormethyl)-1-methyl-N-(3′,4′,5′-trifluor[1,1′-biphenyl]-2-yl)-1H-pyrazol-4-carboxamide. The invention also relates to processes for the production of this crystalline form and formulations for plant protection which contain the crystalline form of 3-(Difluormethyl)-1-methyl-N -(3′,4′,5′-trifluor[1,1′-biphenyl]-2-yl)-1H-pyrazol-4-carboxamide.

摘要翻译： 本发明涉及3-（二甲基甲基）-1-甲基-N-（3'，4'，5'-三氟[1,1'-联苯] -2-基）-1H-吡唑的新结晶形式 -4-甲酰胺。 本发明还涉及生产该结晶形式的方法和用于植物保护的制剂，其含有3-（二甲基甲基）-1-甲基-N-（3'，4'，5'-三氟[ 联苯] -2-基）-1H-吡唑-4-甲酰胺。

公开(公告)号：US20100256418A1

公开(公告)日：2010-10-07

申请号：US12726196

申请日：2010-03-17

申请人： Sebastian Peer SMIDT ,  Jochen Dietz ,  Michael Keil ,  Thomas Grote

发明人： Sebastian Peer SMIDT ,  Jochen Dietz ,  Michael Keil ,  Thomas Grote

IPC分类号： C07C205/04

CPC分类号： C07C201/12 ,  C07C209/68 ,  C07C211/52 ,  C07C205/12

摘要： A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C-6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R.sup.2 radicals may also be different, which comprises reacting the compound of the formula II in which Hal is halogen and X and R1 are as defined above, in the presence of a base and of a palladium catalyst selected from the group of:3 a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic acid (III) in which R2 and n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.

摘要翻译： 制备式I取代的联苯的方法，其中取代基定义如下：X是氟或氯; R1是硝基，氨基或NHR3; R2是氰基，硝基，卤素，C1-C6-烷基，C1-C6-6烯基，C1-C6-炔基，C1-C6-烷氧基，C1-C6-卤代烷基，C1-C6烷基羰基或苯基; R3是C1-C4-烷基，C1-C4-烯基或C1-C4-炔基; n为1,2或3，其中在n为2或3的情况下，R 2基团也可以不同，其包括使其中Hal为卤素且X和R 1的式II化合物与 在碱存在下和选自以下组中的钯催化剂存在下：a）钯 - 三芳基膦或三烷基膦配合物与钯在零氧化状态，b）钯在三芳基膦或三烷基膦存在下的盐 作为络合配体或c）金属钯，任选地在三芳基膦或三烷基膦存在下，在溶剂中与二苯基硼酸（III）反应，其中R 2和n如上所定义，其中使用三芳基膦或三烷基膦 可以被替代。

公开(公告)号：US20100184994A1

公开(公告)日：2010-07-22

申请号：US12664448

申请日：2008-06-13

申请人： Markus Nett ,  Thomas Grote ,  Jan Klaas Lohmann ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Michael Rack ,  Thomas Zierke

发明人： Markus Nett ,  Thomas Grote ,  Jan Klaas Lohmann ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Michael Rack ,  Thomas Zierke

IPC分类号： C07D231/14 ,  C07C229/06

CPC分类号： C07D231/12 ,  C07D231/14

摘要： The present invention relates to a process for preparing 3-difluoromethyl-substituted pyrazole compounds of the formula (I) in which R1 is H, halogen, nitro, C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, phenyl, naphthyl, hetaryl, cyano, —C(═O)—OR1a, —C(═O)—NR1bR1c, —C(═O)—SR1d or —C(═S)—SR1e; R2 is H, C1-C4-alkyl, benzyl or phenyl; R3 is H, halogen, C1-C8-alkoxy, C1-C8-haloalkoxy, C3-C8-cycloalkoxy, C2-C8-alkenyloxy, C1-C8-alkylthio, C1-C8-haloalkylthio, C3-C8-cyclo-alkylthio or C2-C8-alkenylthio; compounds of the formula (II.a) or (II.b), in which R1 and R3 each have one of the definitions given above; R4 is halogen, —OR4a, —SR4a, —O—SO2—R4a or an —NR4bR4c group; R5 and R6 are each C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, benzyl or phenyl, or, together with the nitrogen atom to which they are bonded, are a 3- to 8-membered heterocycle; Lewis acid adducts of compounds of the formula (II.b); the use of compounds of the formula (II.a) or (II.b) and of the Lewis acid adducts for preparing compounds of the formula (I) or (VI); and to a process for converting such compounds to the corresponding 3-difluoro-pyrazol-4-ylcarboxylic acids.

摘要翻译： 本发明涉及制备式（I）的3-二氟甲基取代的吡唑化合物的方法，其中R 1是H，卤素，硝基，C 1 -C 8 - 烷基，C 1 -C 8 - 卤代烷基，C 3 -C 8 - 环烷基， 苯基，萘基，杂芳基，氰基，-C（= O）-OR1a，-C（= O）-NR1bR1c，-C（= O）-SR1d或-C（= S）-SR1e; R2是H，C1-C4-烷基，苄基或苯基; R 3是H，卤素，C 1 -C 8 - 烷氧基，C 1 -C 8 - 卤代烷氧基，C 3 -C 8 - 环烷氧基，C 2 -C 8 - 烯氧基，C 1 -C 8 - 烷硫基，C 1 -C 8 - 卤代烷硫基，C 3 -C 8环 - C 2 -C 8 - 烯硫基; 式（II.a）或（II.b）化合物，其中R 1和R 3各自具有上述定义之一; R4是卤素，-OR4a，-SR4a，-O-SO2-R4a或-NR4bR4c基团; R 5和R 6各自为C 1 -C 8 - 烷基，C 1 -C 8 - 卤代烷基，C 3 -C 8 - 环烷基，苄基或苯基，或与它们所键合的氮原子一起为3-至8-元杂环; 式（II.b）化合物的路易斯酸加合物; 使用式（II.a）或（II.b）化合物和路易斯酸加成物制备式（I）或（VI）化合物的方法; 以及将这些化合物转化为相应的3-二氟 - 吡唑-4-基羧酸的方法。

公开(公告)号：US08188295B2

公开(公告)日：2012-05-29

申请号：US12664448

申请日：2008-06-13

申请人： Markus Nett ,  Thomas Grote ,  Jan Klaas Lohmann ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Michael Rack ,  Thomas Zierke

发明人： Markus Nett ,  Thomas Grote ,  Jan Klaas Lohmann ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Michael Rack ,  Thomas Zierke

IPC分类号： C07D231/14 ,  C07C229/06

CPC分类号： C07D231/12 ,  C07D231/14

摘要： The present invention relates to a process for preparing 3-difluoromethyl-Substituted pyrazole compounds of the formula (I) in which R1 is H, halogen, nitro, C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, phenyl, naphthyl, hetaryl, cyano, —C(═O)—OR1a, —C(═O)—NR1bR1c, —C(═O)—SR1d or —C(═S)—SR1e; R2 is H, C1-C4-alkyl, benzyl or phenyl; R3 is H, halogen, C1-C8-alkoxy, C1-C8-haloalkoxy, C3-C8-cycloalkoxy, C2-C8-alkenyloxy, C1-C8-alkylthio, C1-C8-haloalkylthio, C3-C8-cyclo-alkylthio or C2-C8-alkenylthio; compounds of the formula (II.a) or (II.b), in which R1 and R3 each have one of the definitions given above; R4 is halogen, —OR4a, —SR4a, —O—SO2—R4a or an —NR4bR4c group; R5 and R6 are each C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, benzyl or phenyl, or, together with the nitrogen atom to which they are bonded, are a 3- to 8-membered heterocycle; Lewis acid adducts of compounds of the formula (II.b); the use of compounds of the formula (II.a) or (II.b) and of the Lewis acid adducts for preparing compounds of the formula (I) or (VI); and to a process for converting such compounds to the corresponding 3-difluoro-pyrazol-4-ylcarboxylic acids.

摘要翻译： 本发明涉及一种制备式（I）的3-二氟甲基取代的吡唑化合物的方法，其中R 1是H，卤素，硝基，C 1 -C 8 - 烷基，C 1 -C 8 - 卤代烷基，C 3 -C 8 - 环烷基， 苯基，萘基，杂芳基，氰基，-C（= O）-OR1a，-C（= O）-NR1bR1c，-C（= O）-SR1d或-C（= S）-SR1e; R2是H，C1-C4-烷基，苄基或苯基; R 3是H，卤素，C 1 -C 8 - 烷氧基，C 1 -C 8 - 卤代烷氧基，C 3 -C 8 - 环烷氧基，C 2 -C 8 - 烯氧基，C 1 -C 8 - 烷硫基，C 1 -C 8 - 卤代烷硫基，C 3 -C 8环 - C 2 -C 8 - 烯硫基; 式（II.a）或（II.b）化合物，其中R 1和R 3各自具有上述定义之一; R4是卤素，-OR4a，-SR4a，-O-SO2-R4a或-NR4bR4c基团; R 5和R 6各自为C 1 -C 8 - 烷基，C 1 -C 8 - 卤代烷基，C 3 -C 8 - 环烷基，苄基或苯基，或与它们所键合的氮原子一起为3-至8-元杂环; 式（II.b）化合物的路易斯酸加合物; 使用式（II.a）或（II.b）化合物和路易斯酸加成物制备式（I）或（VI）化合物的方法; 以及将这些化合物转化为相应的3-二氟 - 吡唑-4-基羧酸的方法。

公开(公告)号：US08030527B2

公开(公告)日：2011-10-04

申请号：US12726196

申请日：2010-03-17

申请人： Sebastian Peer Smidt ,  Jochen Dietz ,  Michael Keil ,  Thomas Grote

发明人： Sebastian Peer Smidt ,  Jochen Dietz ,  Michael Keil ,  Thomas Grote

IPC分类号： C07C205/06

CPC分类号： C07C201/12 ,  C07C209/68 ,  C07C211/52 ,  C07C205/12

摘要： A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C-6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R.sup.2 radicals may also be different, which comprises reacting the compound of the formula II in which Hal is halogen and X and R1 are as defined above, in the presence of a base and of a palladium catalyst selected from the group of:3 a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic acid (III) in which R2 and n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.

摘要翻译： 制备式I取代的联苯的方法，其中取代基定义如下：X是氟或氯; R1是硝基，氨基或NHR3; R2是氰基，硝基，卤素，C1-C6-烷基，C1-C6-6烯基，C1-C6-炔基，C1-C6-烷氧基，C1-C6-卤代烷基，C1-C6-烷基羰基或苯基; R3是C1-C4-烷基，C1-C4-烯基或C1-C4-炔基; n为1,2或3，其中在n为2或3的情况下，R 2基团也可以不同，其包括使其中Hal为卤素且X和R 1的式II化合物与 在碱存在下和选自以下组中的钯催化剂存在下：a）钯 - 三芳基膦或三烷基膦配合物与钯在零氧化状态，b）钯在三芳基膦或三烷基膦存在下的盐 作为络合配体或c）金属钯，任选地在三芳基膦或三烷基膦存在下，在溶剂中与二苯基硼酸（III）反应，其中R 2和n如上所定义，其中使用三芳基膦或三烷基膦 可以被替代。

公开(公告)号：US07709684B2

公开(公告)日：2010-05-04

申请号：US12087345

申请日：2007-05-31

申请人： Sebastian Peer Smidt ,  Jochen Dietz ,  Michael Keil ,  Thomas Grote

发明人： Sebastian Peer Smidt ,  Jochen Dietz ,  Michael Keil ,  Thomas Grote

IPC分类号： C07C211/45 ,  C07C211/48 ,  C07C205/06

CPC分类号： C07C201/12 ,  C07C209/68 ,  C07C211/52 ,  C07C205/12

摘要： A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R2 radicals may also be different, which comprises reacting the compound of the formula II in which Hal is halogen and X and R1 are as defined above, in the presence of a base and of a palladium catalyst selected from the group of: a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic acid (III) in which R2 and n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.

摘要翻译： 制备式I取代的联苯的方法，其中取代基定义如下：X是氟或氯; R1是硝基，氨基或NHR3; R2是氰基，硝基，卤素，C1-C6-烷基，C1-C6-烯基，C1-C6-炔基，C1-C6-烷氧基，C1-C6-卤代烷基，C1-C6-烷基羰基或苯基; R3是C1-C4-烷基，C1-C4-烯基或C1-C4-炔基; n为1,2或3，其中在n为2或3的情况下，R2基团也可以不同，其包括使Hal为卤素的化合物与X和R 1如上所定义的化合物反应在 存在碱和钯催化剂，其选自：a）钯 - 三芳基膦或三烷基膦配合物与钯在零氧化状态，b）钯在三芳基膦或三烷基膦作为络合配体存在下的盐，或 c）金属钯，任选地在三芳基膦或三烷基膦存在下，在溶剂中与其中R 2和n如上定义的二苯基硼酸（III）反应，其中所用的三芳基膦或三烷基膦可以被取代。

公开(公告)号：US08115012B2

公开(公告)日：2012-02-14

申请号：US12513003

申请日：2007-11-02

申请人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

发明人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

IPC分类号： C07D231/10 ,  C07F7/08

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylates of the formula I in which R1 is C1-C8-alkyl, C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, etc.; and R2 is hydrogen, C1-C4-alkyl, benzyl or phenyl, wherein a) a compound of the general formula II in which X is fluorine, chlorine or bromine, R1 has one of the meanings given above and R4 is C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, benzyl or phenyl, is reacted with a silane compound of the general formula R3nSiCl(4-n) in which n is 1, 2 or 3 and the substituents R3 are independently of one another selected from the group consisting of C1-C8-alkyl and phenyl and with a metal selected from the metals of groups 1, 2, 3, 4 and 12 of the Periodic Table of the Elements having a redox potential of less than −0.7 V, based on a normal hydrogen electrode (at 25° C. and 101.325 kPa); and b) the reaction mixture from step a) is reacted with a compound of the general formula III R2HN—NH2  (III) in which R2 has one of the meanings given above.

摘要翻译： 本发明涉及制备式Ⅰ的二氟甲基取代的吡唑-4-基羧酸酯的方法，其中R 1是C 1 -C 8烷基，C 3 -C 8环烷基，C 1 -C 4烷氧基-C 1 -C 4烷基等 。 R 2是氢，C 1 -C 4 - 烷基，苄基或苯基，其中a）通式II的化合物，其中X是氟，氯或溴，R 1具有上面给出的含义之一，R 4是C 1 -C 8 - 烷基，C 3 -C 8 - 环烷基，C 2 -C 8 - 烯基，苄基或苯基与通式R 3 n SiCl（4-n）的硅烷化合物反应，其中n为1,2或3，取代基R 3独立地为 选自由C 1 -C 8 - 烷基和苯基组成的组中的一种，以及选自元素周期表第1,2,3,4和12族金属的金属，其氧化还原电位小于-0.7 V，基于正常的氢电极（在25℃和101.325kPa）; 和b）将来自步骤a）的反应混合物与通式III的化合物R2HN-NH2（III）反应，其中R2具有上述含义之一。

公开(公告)号：US20100069646A1

公开(公告)日：2010-03-18

申请号：US12513003

申请日：2007-11-02

申请人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

发明人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

IPC分类号： C07D231/10 ,  C07F7/08

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylates of the formula I in which R1 is C1-C8-alkyl, C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, etc.; and R2 is hydrogen, C1-C4-alkyl, benzyl or phenyl, wherein a) a compound of the general formula II in which X is fluorine, chlorine or bromine, R1 has one of the meanings given above and R4 is C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, benzyl or phenyl, is reacted with a silane compound of the general formula R3nSiCl(4-n) in which n is 1, 2 or 3 and the substituents R3 are independently of one another selected from the group consisting of C1-C8-alkyl and phenyl and with a metal selected from the metals of groups 1, 2, 3, 4 and 12 of the Periodic Table of the Elements having a redox potential of less than −0.7 V, based on a normal hydrogen electrode (at 25° C. and 101.325 kPa); and b) the reaction mixture from step a) is reacted with a compound of the general formula III R2HN—NH2   (III) in which R2 has one of the meanings given above.

摘要翻译： 本发明涉及制备式Ⅰ的二氟甲基取代的吡唑-4-基羧酸酯的方法，其中R 1是C 1 -C 8烷基，C 3 -C 8环烷基，C 1 -C 4烷氧基-C 1 -C 4烷基等 。 并且R 2是氢，C 1 -C 4 - 烷基，苄基或苯基，其中a）通式II的化合物，其中X是氟，氯或溴，R 1具有上面给出的含义之一，R 4是C 1 -C 8 - 烷基，C 3 -C 8 - 环烷基，C 2 -C 8 - 烯基，苄基或苯基与通式R 3 n SiCl（4-n）的硅烷化合物反应，其中n为1,2或3，取代基R 3独立地为 选自由C 1 -C 8 - 烷基和苯基组成的组中的一种，以及选自元素周期表第1,2,3,4和12族金属的金属，其氧化还原电位小于-0.7 V，基于正常的氢电极（在25℃和101.325kPa）; 和b）将来自步骤a）的反应混合物与通式III的化合物R2HN-NH2（III）反应，其中R2具有上述含义之一。

公开(公告)号：US20090005597A1

公开(公告)日：2009-01-01

申请号：US12087345

申请日：2007-05-31

申请人： Sebastian Peer Smidt ,  Jochen Dietz ,  Michael Keil ,  Thomas Grote

发明人： Sebastian Peer Smidt ,  Jochen Dietz ,  Michael Keil ,  Thomas Grote

IPC分类号： C07C201/12 ,  C07C209/68

CPC分类号： C07C201/12 ,  C07C209/68 ,  C07C211/52 ,  C07C205/12

摘要： A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R2 radicals may also be different, which comprises reacting the compound of the formula II in which Hal is halogen and X and R1 are as defined above, in the presence of a base and of a palladium catalyst selected from the group of: a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic acid (III) in which R2 and n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.

摘要翻译： 制备式I取代的联苯的方法，其中取代基定义如下：X是氟或氯; R1是硝基，氨基或NHR3; R2是氰基，硝基，卤素，C1-C6-烷基，C1-C6-烯基，C1-C6-炔基，C1-C6-烷氧基，C1-C6-卤代烷基，C1-C6-烷基羰基或苯基; R3是C1-C4-烷基，C1-C4-烯基或C1-C4-炔基; n为1,2或3，其中在n为2或3的情况下，R2基团也可以不同，其包括使Hal为卤素的化合物与X和R 1如上所定义的化合物反应在 存在碱和钯催化剂，其选自：a）钯 - 三芳基膦或三烷基膦配合物与钯在零氧化状态，b）钯在三芳基膦或三烷基膦作为络合配体的存在下的盐，或 c）金属钯，任选地在三芳基膦或三烷基膦存在下，在溶剂中与其中R 2和n如上定义的二苯基硼酸（III）反应，其中所用的三芳基膦或三烷基膦可以被取代。