IP Library Granted Patent US 7,820,830
Granted Patent B2
US 7,820,830 · App. 12/093,619 · Granted Oct 26, 2010

Process for the production of carboxanilides

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Quick Facts
Patent No.
US 7,820,830
App. No.
12/093,619
Granted
Oct 26, 2010
Kind
B2
Abstract

The present invention relates to a novel process for the preparation of a compound of general formula (I): wherein R 1 is H or C 1-4 alkyl and R 2 is difluoromethyl or trifluoromethyl, which comprises reacting a compound of general formula (II): wherein R 1 has the meaning given above and X is chloro or bromo, with a compound of general formula (III): wherein R 2 has the meaning given above, in the presence of a base, a palladium catalyst and a ferrocenyl biphoshine ligand of the Josiphos type, the reaction being carried out in an ether solvent at a reflux temperature of at least 100° C.

Claims (13)

1. A process for the preparation of the compound of the general formula (I):

wherein R 1 is H or C 1-4 alkyl and R 2 is difluoromethyl or trifluoromethyl, which comprises reacting the compound of the general formula (II):

wherein R 1 has the meaning given above and X is chloro or bromo, with a compound of the general formula (III):

wherein R 2 has the meaning given above, in the presence of a base, a palladium catalyst and a ferrocenyl biphoshine ligand of the Josiphos type, the reaction being carried out in an ether solvent at a reflux temperature of at least 100° C.

2. A process according to claim 1 wherein X is chloro.

3. A process according to claim 1 wherein the base is a hydroxide or carbonate of sodium, potassium, cesium, lithium, calcium or barium, the phosphates of sodium or potassium or the C 1 -C 4 alkoxide of sodium or potassium.

4. A process according to claim 1 wherein the palladium catalyst is palladium dichloride, palladium(II) acetate, tris-dibenzylideneacetone-dipalladium or bis-dibenzylideneacetone palladium.

5. A process according to claim 1 wherein the ligand is (R)-(−)-1-[(S)-2-(dicyclohexylphosphino)-ferrocenyl]ethyldi-tert-butylphosphine having the structural formula:

6. A process according to claim 1 wherein the solvent is diethyleneglycol dialkylethers having the general formula:

ROCH 2 CH 2 OCH 2 CH 2 OR

wherein R is C 1-4 alkyl.

7. A process according to claim 5 wherein the solvent is di(ethylene glycol) dimethyl ether.

8. A process according to claim 1 wherein the reaction is carried out at a temperature of from 130 to 200° C.

Assignments (2)
MERGER Recorded Aug 14, 2025
From: SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 072459/0644 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2010
From: WALTER, HARALD; EHRENFREUND, JOSEF; CORSI, CAMILLA; TOBLER, HANS
To: SYNGENTA CROP PROTECTION, INC.
Reel/Frame 024603/0053 →