Allyl Mercaptan → Methyl 4-bromo-2-(2-propenylsulphenylmethyl)benzoate

Participants

Reaction Steps

Methyl 4-bromo-2-bromomethylbenzoate (24.6 g) was added to a stirred mixture of allylmercaptan (70%, 9 g), sodium ethoxide (5.77 g) and tetrabutylammonium iodide (0.4 g) for 15 minutes. Cold sodium bicarbonate solution was added and the mixture extracted with ether. The extract was washed with brine, dried (magnesium sulphate) and evaporated to give methyl 4-bromo-2-(2-propenylsulphenylmethyl)benzoate (2.41 g), NMR (CDCl3) 3.05 (d,2H), 3.9 (s,3H), 4.0 (s,2H), 5.1 (m,2H), 5.75 (m,1H), 7.4 (d,1H), 7.5 (s,1H), 7.75 (d,1H).

Provenance & Evidence