4-Chlorobenzyl mercaptan → HCID 69515471, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of n-BuLi (2.5M, 11.5 mL, 28.8 mmol) in THF (20 mL) at 0° C. is added (4-Chloro-phenyl)-methanethiol (4 mL, 30 mmol) dropwise over 15 min. After 1 hr., a solution of 18 (2 g, 6 mmol) in THF (15 mL) is added. The reaction is then stirred at 0° C. for 1 hour and 2 hrs. at room temperature. The reaction was then quenched with water and extracted with EtOAc (3×50 mL). The combined organics are then washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (3% EtOAc/hexane) provides 19 (1.98 g, 80%) as a white solid. 1H NMR (CDCl3): δ 10.00 (1H, br. s), 7.29 (2H, d, J=8.4 Hz), 7.25 (2H, d, J=8.4 Hz), 4.36 (2H, s), 3.89 (3H, s), 1.53 (9H, s).

Provenance & Evidence