Hydrochloric Acid → HCID 86685089, compound

Participants

Reaction Steps

To a solution of 4-fluoro-3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (970 mg, 5 mmol) in CCl4 (50 mL) at rt was added benzoyl peroxide (121 mg, 0.5 mmol) followed by NBS (1.958 g, 11.0 mmol). The reaction mixture was heated under reflux for 16 h, cooled to rt and treated with Na2CO3. The aqueous layer was acidified with 3 N HCl to pH 3 and extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried over with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (2:1) to give 4-fluoro-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde (688 mg, 68%) as a light yellow solid.

Provenance & Evidence