N-bromobutanimide → 3'-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester

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Reaction Steps

3′-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester was synthesized as described for 4′-bromomethyl-biphenyl-3-carboxylic acid ethyl ester. 3′-Methyl-biphenyl-4-carboxylic acid ethyl ester (3.80 g, 15.81 mmol, 1 eq.) in carbon tetrachloride was treated with N-bromosuccinimide (3.1 g, 17.39 mmol, 1.1 eq.) and 2,2′-azobisisobutyronitrile (0.13 g, 0.79 mmol, 5 mol %). When complete, the reaction was worked up as described leaving 3′-bromomethyl-biphenyl-4-carboxylic acid ethyl ester (4.83 g, 96%) as a yellow oil that crystallized on standing.

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