4-Bromoanisole → HCID 86675423, compound

Participants

Reaction Steps

In a 500 mL 3-neck round bottom flask equipped with reflux condenser, N2 inlet, thermometer socket and magnetic bar inside was added 4-Methoxy-3-(2,2,2-trifluoroacetylamino)benzenesulfonyl chloride (17 grams, 53.5 mmol) in 1,2-dichloroethane (200 mL). To the stirred solution of above reactions mass, Aluminium chloride (7.86 grams, 58.89 mmol) and 4-bromo anisole (20 grams, 107 mmol) were added slowly. Then the reaction mass was stirred under reflux temperature for 20 hours. Reaction mass was quenched into ice cold water and acidified with 2N hydrochloric acid (50 mL) until the pH was ˜4 and extracted the product with ethyl acetate (3×200 mL). The combined organic layers were washed with brine solution (1×50 mL), dried over anhydrous sodium sulfate and solvent was removed under reduced pressure to obtain the technical product. It was further purified by column chromatography to obtain the title product, the eluent being 15% ethyl acetate in n-hexane. Yield: 18.4 grams

Provenance & Evidence