Dimethyl Disulfide → HCID 10058722, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2.5M in hexane, 35 ml) was added with cooling to a solution of 3,4-difluorobenzoic acid (5.5 g) in dry tetrahydrofuran under an inert atmosphere maintaining the temperature below -70° C. The mixture was stirred for 2 hours at -70° C. A solution of dimethyl disulfide (19.8 g) in tetrahydrofuran was added and the mixture was stirred at -70° C. for 1.5 hours. It was allowed to warm to room temperature, diluted with ether and washed with water. The aqueous layer was acidified to pH 1, extracted with ether, washed with water, dried (anhydrous MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was recrystallized from a mixture of cyclohexane and ether to give 3,4-difluoro-2-(methylsulfenyl)benzoic acid (5.9 g) as a white solid, m.p. 149.2°-149.6° C.

Provenance & Evidence