N-bromobutanimide → 6-(bromomethyl)-1H-spiro[benzo[c][1,2]oxaborole-3,1'-cyclopentan]-1-ol

Participants

Reaction Steps

To a solution of 6-methyl-1H-spiro[benzo[c][1,2]oxaborole-3,1′-cyclopentan]-1-ol (1.2 g, 6.0 mmol) in CCl4 (10 mL) under nitrogen was added NBS (1.07 g, 6.0 mmol) and BPO (145 mg, 0.6 mmol). The mixture was heated at reflux for 2 h under the light from a Sun lamp, and then it was cooled to rt, washed with aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under vacuum. The residue was purified on column chromatography to provide the product (1.2 g, yield 71.7%).

Provenance & Evidence