N-bromobutanimide → 4'-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester

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Reaction Steps

4′-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester was prepared as described for 4′-bromomethyl-biphenyl-3-carboxylic acid ethyl ester. 4′-Methyl-biphenyl-4-carboxylic acid ethyl ester (3.4 g, 14.15 mmol, 1 eq.) was reacted with N-bromosuccinimide (3.27 g, 18.4 mmol, 1.3 eq.) and 2,2′-azobisisobutyronitrile (0.12 g, 0.71 mmol, 5 mol %) in carbon tetrachloride (150 mL). When complete, the reaction was worked up as described to produce 4′-bromomethyl-biphenyl-4-carboxylic acid ethyl ester (3.74 g, 83% yield) as a yellow solid.

Provenance & Evidence