Boron tribromide → HCID 22728130, compound

Participants

Reaction Steps

To a solution of N-Cyclobutyl-5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonamide (451 mg, 1.0 mmol) in methylene chloride (9 mL) at 0° C. was added boron tribromide (1M in methylene chloride, 2.0 mL, 2.0 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction was quenched with water (25 mL) and stirred at room temperature for 1 hour, then extracted with ethyl acetate (3 times 40 mL). The combined organic extracts were washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (5% ethyl acetate in CH2Cl2) to afford the title compound (403 mg). 1H NMR (400 MHz, CDCl3) δ8.39 (s, 1H), 8.28 (s, 2H), 7.05-6.94 (m, 3H), 4.77 (d, 1H), 3.77-3.71 (m, 1H), 2.14-2.07 (m, 2H), 1.75-1.56 (m, 4H). MS (APCI−) Calc: 432.1, Found: 431.2 (M−1).

Provenance & Evidence