4-Bromoanisole → HCID 118207413, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-4-methoxybenzene (0.88 g, 4.7 mmol) in THF (50 mL) was added n-butyllithium (2.9 mL, 4.7 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 2 h, then added to a flask containing tert-butyl 4-oxoazepane-1-carboxylate (1 g, 4.7 mmol) in THF, cooled to −78° C. The reaction mixture was stirred at −78° C. for 30 min and then at 0° C. for 15 min. It was then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as the eluant to yield tert-butyl 4-hydroxy-4-(4-methoxyphenyl)azepane-1-carboxylate (0.68 g, 45%). LCMS: R.T. 0.96 min. LCMS (ES-API), m/z 320 (M−H).

Provenance & Evidence