Benzyl Bromide → HCID 20205048, compound

Participants

Reaction Steps

A solution of S-2-carbomethoxy-3-methoxyphenyl dimethylthiocarbamate (1.2 g, 4.5 mmol) and sodium methoxide (0.24 g, 4.5 mmol) in methanol (10 ml) was stirred at reflux temperature under a nitrogen atmosphere for 4 hours. α-Bromotoluene (0.60 ml, 4.9 mmol) was then added, and heating was maintained for an additional hour. The cooled mixture was evaporated, and the residue partitioned between diethyl ether and water. The organic layer was separated and washed with 1% aqueous sodium hydroxide solution, water, saturated aqueous sodium chloride solution, dried (sodium sulfate), and evaporated. The residue was vacuum filtered through a pad of silica gel (Merck No. 7734), eluting successively with 10:1 and 5:1 hexane-ether. Evaporation of the appropriate fractions gave methyl 2-benzylthio-6-methoxybenzoate as a colorless syrup; yield (0.70 g, 54%); NMR (CDCl3, 60 MHz): δ4.06 (s, SCH2Ph) p.p.m.

Provenance & Evidence