Hydrochloric Acid → HCID 22036226, compound

Participants

Reaction Conditions

Reaction Steps

To 3-Bromobenzenethiol (1.6 mL, 13.5 mmol) in THF (10 mL) at 0° C. was added sodium hydride (60 wt %, 600 mg, 14.9 mmol). After stirring for 10 minutes, the reaction was cooled to −78° C. and n-butyllithium (7.4 mL, 14.9 mmol) was added dropwise. After stirring for 20 minutes, 3-pentanone (1.6 mL, 14.9 mmol) was added, and the reaction was slowly warmed to room temperature and immediately acidified with 1N aqueous HCl to pH 3. The reaction mixture was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (5% EtOAc in hexanes) to give the desired product, 10l.

Provenance & Evidence