tert-Butanol → tert-butyl 2-(2-bromophenyl)acetate

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Reaction Steps

A mixture of 2-bromophenylacetic acid (5.02 g), N,N-dicyclohexylcarbodiimide (5.3 g), 4-pyrrolidinopyridine (0.4 g) and t-butanol (1.74 g) in DCM (120 ml) was stirred at room temperature, under nitrogen, for 4 h. The mixture was left to stand for 18 h, then ER (150 ml) was added and the mixture was filtered and washed with ER. The filtrate was evaporated in vacuo to leave a yellow suspension. F.C.C. (A) eluting with hexane gave a white semisolid, which was further chromatographed eluting with hexane, then 1% ER in hexane, and finally 2% gave a colorless liquid. Vacuum distillation by Kugelrohr at 0.4 mmHg and at 140°-150° gave the title compound as a colorless oil (0.55 g). T.l.c. (A) hexane:ER (3:1) Rf 0.68.

Provenance & Evidence