2-Methylthiophene → Triphenyl(2-thienylmethyl)phosphonium Bromide

Participants

Reaction Steps

A mixture of 2-methylthiophene (10 g, 0.10 mol) and N-bromosuccinimide (18 g, 0.10 mol) in carbon tetrachloride (100 ml) was heated to reflux under nitrogen. Benzoyl peroxide (50 mg) was added and the mixture was refluxed for 3 hours. After cooling to room temperature the reaction was filtered and concentrated to a dark oil. The crude 2-bromomethylthiophene and triphenylphosphine (29 g, 0.011 mol) were dissolved in tetrahydrofuran (170 ml) under nitrogen and heated to reflux for 4 hours and then cooled to room temperature for precipitation. The product was collected by filtration, washed with ethyl ether (4×15 ml) and dried to afford (2-thienyl)methyl triphenylphosphonium bromide (35 g, 80%). m.p. 250° C.

Provenance & Evidence