Diethyl Ether → 4-Bromo-2-fluoro-alpha,alpha-dimethylbenzenemethanol

Participants

Reaction Steps

To a solution of methyl 4-bromo-2-fluorobenzoate (12 g, 51.5 mmol) in anhydrous ether (140 mL) at 0° C. was added MeMgBr (3.0 M, 70 g) dropwise. The mixture was slowly warmed up to room temperature and stirred for 3 hours. The reaction was quenched by the addition of saturated NH4Cl and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with brine, dried with Na2SO4 and evaporated to dryness. The mixture was purified by flash column chromatography (0–20% EtOAc in hexanes) to give the product (12 g, 95% yield). 1H NMR (300 MHz, CDCl3) δ: 1.62 (s, 6 H), 7.18–7.23 (m, 1 H), 7.25–7.28 (m, 1 H), 7.44–7.49 (m, 1 H).

Provenance & Evidence