4-Toluenesulfonyl chloride → HCID 57445087, compound

Participants

Reaction Steps

Add potassium hydroxide (1.15 g, 17.5 mmol, fresh powder) to a solution of tert-butyl 2-(2-bromo-4-fluorophenyl)-2-hydroxyethylcarbamate (1.19 g, 3.56 mmol) and p-toluenesulfonyl chloride (0.75 g, 3.88 mmol) in dry THF (50 mL). Stir the mixture overnight at RT. Dilute with DCM, and wash with water and aqueous saturated sodium chloride. Dry over sodium sulfate and concentrate. Purify by column chromatography (hexane to 5% ethyl acetate in hexane) to give the title compound as a colorless oil (0.46 g, 41%). 1H NMR (400 MHz, CD3Cl) δ 1.47 (s, 9H), 2.08 (d, J=3.2 Hz, 1H), 2.67 (d, J=5.6 Hz, 1H), 3.59 (dd, J=3.6 Hz, 6.0 Hz, 1H), 7.00 (m, 1H), 7.28 (m, 1H), 7.35 (m, 1H).

Provenance & Evidence