N-bromobutanimide → Ethyl 4'-(bromomethyl)-[1,1'-biphenyl]-2-carboxylate

Participants

Reaction Steps

4′-Bromomethyl-biphenyl-2-carboxylic acid ethyl ester was prepared in a similar fashion to 4′-bromomethyl-biphenyl-3-carboxylic acid ethyl ester as described. 4′-Methyl-biphenyl-2-carboxylic acid ethyl ester (5.58 g, 23.22 mmol, 1 eq.) in carbon tetrachloride was treated with N-bromosuccinimide (4.96 g, 27.86 mmol, 1.2 eq.) and 2,2′-azobisisobutyronitrile (0.19 g, 1.16 mmol, 5 mol %). When complete, the reaction was worked up as described to give a yellow oil. The oil was purified by silica gel flash chromatography using 5% EtOAc in hexane as the mobile phase. Fractions containing the product were pooled and the solvent removed in vacuo to give 4′-bromomethyl-biphenyl-2-carboxylic acid ethyl ester (7.32 g, 99% yield) as a yellow oil.

Provenance & Evidence