Sodium hydride → 5-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran

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Reaction Steps

To a stirred, cooled (ice bath) suspension of sodium hydride (60% dispersion in mineral oil, 0.024 g, 0.6 mmol) in 10 mL of anhydrous tetrahydrofuran under argon, a solution of 4-bromo-2-(2-chloro-1,1-dimethyl-ethyl)phenol (Intermediate 1, 0.13 g, 0.5 mmol) in 2 mL of anhydrous tetrahydrofuran was added. After 0.5 h, the excess sodium hydride was quenched with methanol and the reaction mixture was evaporated in vacuo. The residue was diluted with water, extracted with ether and the organic phase was washed with brine. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to an oil. Flash column chromatography of the oil over silica gel (230-400 mesh) using 2.5% ethyl acetate in hexane as the eluent afforded the title compound as a pale yellow oil (0.085 g, 75.7%).

Provenance & Evidence