Methanol → Methyl 4-(1-bromoethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

A solution of trimethylsillyldiazomethane in THF (2M, 49.1 mL, 98.3 mmol) was added dropwise to a solution of 4-(1-bromoethyl)benzoic acid (15 g, 66 mmol) in methanol (75 mL) and THF (75 mL) at 0° C. The resulting mixture was stirred at 23° C. for 3 h, then concentrated and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution (2×). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound. 1H NMR (400 MHz, CDCl3): δ 8.02 (d, 2H, J=8.5 Hz), 7.51 (d, 2H, J=8.2 Hz), 5.21 (q, 1H, J=6.7 Hz), 3.92 (s, 3H), 2.06 (d, 3H, J=7.0 Hz).

Provenance & Evidence