2-Bromobenzoyl chloride → 1-(2-broMophenyl)-2-Methylpropan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromobenzoyl chloride (1.3 mL, 9.9 mmol) in dry tetrahydrofuran (38 mL) at 0° C. under nitrogen was added dropwise a 2.0 M solution of isopropylmagnesium bromide in tetrahydrofuran (12.4 mL, 24.8 mmol) over ca. 5 minutes. The reaction mixture was stirred at 0° C. for 30 minutes then at room temperature for 27 hours. The reaction was quenched by the addition of 1 M aqueous hydrochloric acid (30 mL) and concentrated in vacuo to remove tetrahydrofuran. The aqueous phase was diluted to ca. 50 mL with water and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the crude product as an orange oil (2.1 g). Purification by flash chromatography using a solvent gradient of 1 to 4% ethyl acetate in hexane gave the title compound (0.77 g, 33%) as a clear, pale yellow oil.

Provenance & Evidence