Hydrochloric Acid → HCID 86685509, compound

Participants

Reaction Steps

To a solution of 5-chloro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (540 mg, 2.57 mmol) in CCl4 (30 mL) at rt was added benzoyl peroxide (62 mg, 0.26 mmol) followed by NBS (915 mg, 5.14 mmol). The reaction mixture was refluxed for 16 h, cooled to rt and treated with Na2CO3. The aqueous layer was acidified with 3 N HCl to pH of 3 and extracted with EA. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with DCM-MeOH (20:1) to give 5-chloro-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde (310 mg; yield 53.8%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.38 (s, 1H), 9.41 (s, 1H), 8.22 (s, 1H), 7.82 (s, 1H), 1.50 (s, 6H) ppm; MS: m/z=224.9 (M+1, ESI+).

Provenance & Evidence