Triphenylphosphine → 2-Cyanomethoxy-3-methylbenzyl bromide

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (15.2 g, 57.8 mmoles) is added to 2-cyanomethoxy-3-methylbenzylalcohol (9.3 g, 52.5 mmoles, example 23) in THF (175 mL). The mixture is stirred until homogeneous and cooled to 0° C., followed by addition, in three portions, of N-bromosuccinimide (10.3 g, 57.8 mmoles). After 90 minutes the reaction is concentrated and the residue purified by column chromatography (silica, 5:1 hex: EtOAc) to yield the title compound as a pale yellow crystalline solid. MS (EI) 239, 241 (M)+, Br pattern.

Provenance & Evidence