Benzyl Bromide → 4-benzyl-6-bromo-spiro[3H-1,4-benzoxazine-2,1-cyclopropane]

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-bromospiro[3,4-dihydro-1,4-benzoxazine-2,1′-cyclopropane] (3.11 g, 12.9 mmol) in DMF (20 mL) was added potassium carbonate (3.6 g, 26.0 mmol) and benzyl bromide (1.61 mL, 13.6 mmol). The reaction mixture was heated at 60° C. for 6 h then cooled to room temperature and quenched by the addition of water. The reaction mixture was extracted with ethylacetate (2×50 mL) and the combined organic layers were washed with water (20 mL) and brine (20 mL), then dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography to furnish 4-benzyl-6-bromo-spiro[3H-1,4-benzoxazine-2,1-cyclopropane] (1.13 g).

Provenance & Evidence