Benzyl Bromide → HCID 11773762, compound

Participants

Reaction Steps

To a solution of 6-bromo-9-(phenylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-ol (25 mg, 0.06 mmol) in N,N-dimethylformamide (2 mL) was added benzyl bromide (0.5 mL) and sodium hydride (60% in oil, 50 mg, 1.2 mmol). The reaction was stirred 1.0 min and quenched with water (1 mL). The reaction was diluted with ethyl acetate, washed with water, and concentrated to provide 6-bromo-1-[(phenylmethyl)oxy]-9-(phenylsulfonyl)-2,3,4,9-tetrahydro-1H-carbolzole: MS m/z (m−1) 494, 496. The crude benzyl ether was dissolved in methanol (5 mL) and tetrahydrofuran (3 mL) and aqueous sodium hydroxide (5N, 2 mL) and sodium hydroxide pellets (300 mg, 1.1 mmol) were added. The reaction was stirred at 70° C. for 16 h. The reaction was concentrated, diluted with ethyl acetate, washed with water and concentrated. The crude ether was purified by flash chromatography on silica (5% to 10% ethyl acetate/hexanes) to provide 6-bromo-1-[(phenylmethyl)oxy]-2,3,4,9-tetrahydro-1H-carbazole (15 mg, 71%). as an oily white solid: 1H-NMR (DMSO-d6): δ 11.10 (s, 1H), 7.57 (s, 1H), 7.39 (d, 2H), 7.33 (t, 2H), 7.29-7.24 (d, 2H), 7.13 (d, 1H), 4.72-4.61 (m, 3H), 2.69-2.63 (m, 1H), 2.55-2.50 (m, 1H), 1.99-1.91 (m, 3H), 1.78-1.71 (m, 1H); MS m/z (M−1) 354, 356.

Provenance & Evidence