Carbon tetrabromide → 5-(Bromomethyl)furan-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

38 g (145 mmol) triphenylphosphine were added to a solution of 15 g (121 mol [sic]) of 5-hydroxymethyl-2-cyanofuran in 250 ml of tetrahydrofuran. The mixture was cooled to -10° C., and a solution of 48 g (145 mmol) of tetrabromomethane in 100 ml of tetrahydrofuran was added. The mixture was allowed to warm to room temperature and was stirred at this temperature for 3 hours. The mixture was concentrated in a rotary evaporator under water pump vacuum and the residue was purified by column chromatography (mobile phase petroleum ether:dichloromethane 1:1, Rf =0.5). 11.5 g of the title compound were obtained. 1H-NMR (250 MHz, d6 -DMSO): δ=4.8 (m, 2H), 6.7 (d, 1H), 7.7 (d, 1H).

Provenance & Evidence