Toluene → 1-(4-Bromophenyl)-2-methylpropan-2-ol

Participants

Reaction Conditions

Reaction Steps

A solution of bromo(methyl)magnesium in diethyl ether (25 mL of 3 M, 74.5 mmol) in THF (8 mL) and toluene (25 mL) was added to a solution of ethyl 2-(4-bromophenyl)acetate (8.23 g, 33.9 mmol) in Et2O (165 mL) and the reaction mixture was stirred at 40° C. for 1 hour. The reaction mixture was quenched by the addition of saturated aqueous ammonium chloride (200 mL) and the phases were separated. The organics were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography eluting with 0-30% EtOAc-hexanes to give 1-(4-bromophenyl)-2-methyl-propan-2-ol (5.68 g, 73%), as a clear oil. ESI-MS m/z calc. 228.1. Found 229.5 (M+1)+; Retention time: 1.45 minutes (3 min run).

Provenance & Evidence