Oxalyl chloride → HCID 18003808, compound

Participants

Reaction Steps

2,4-Difluoro-3-methoxybenzoic acid (38.2 g) was added to a stirred solution of methyl mercaptan (9.7 g) in dry tetrahydroftran under an inert atmosphere. A solution of n-butyl lithium (162 ml of a 2.5M solution in hexane) was added dropwise at −78° C. After 1 hour the mixture was allowed to warm to 20° C. overnight and evaporated. Hydrochloric acid (2M) and ether were added and the organic phase washed (water), dried mil (magnesium sulphate) and evaporated. The residue was triturated with hexane to give 4-fluoro-3-methoxy-2-methylthiobenzoic acid (29.2 g), NMR 2.6 (s, 3H), 4.0 (s, 3H), 7.1 (m, 1H), 7.9 (m, 1H). oxalyl chloride (51.5 g) was added to a stirred solution of 4-fluoro-3-methoxy-2-methylthiobenzoic acid (29.2 g) in dichloromethane. After 3.5 hours the mixture was evaporated to give the title compound (33.0 g), used directly in the above reactions.

Provenance & Evidence