Methyl chlorodifluoroacetate → 4-Chloro-2-trifluoromethyl-6-methyl-benzoic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Methyl chlorodifluoroacetate	HCID 73935	—
Reactant	Potassium Fluoride	HCID 522689	—
Reactant	Methyl 4-chloro-2-iodo-6-methylbenzoate	HCID 67192903	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-Chloro-2-trifluoromethyl-6-methyl-benzoic acid methyl ester	HCID 57949432	67.4%

Reaction Conditions

Temperature	140 °C

Reaction Steps

CuI (1.9 g, 10 mmol) and potassium fluoride (0.58 g, 10 mmol) were added under an N2 atmosphere to a solution of 4-chloro-2-iodo-6-methyl-benzoic acid methyl ester (2.9 g, 9.4 mmol) and chloro-difluoro-acetic acid methyl ester (1.2 mL, 11 mmol) in DMF (25 mL). The mixture was stirred at 140° C. for 18 h. The reaction was cooled and the solvent evaporated. Silica gel column chromatography using 10% ethyl acetate in hexane afforded 4-chloro-2-trifluoromethyl-6-methyl-benzoic acid methyl ester (1.6 g, 67%). GC-MS: m/z 252 (M−1)+, 221 (M−31)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07968570B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-14fd7c9cdfb9490286d98954739ab7a0
Source note	uspto-grants-2011_06