Aluminum(III) Chloride → HCID 59192513, compound

Participants

Reaction Steps

To a stirred solution of 7-chloro-6-fluoro-5-methoxy-3,4-dihydro-2H-naphthalen-1-one (1.04 g, 4.7 mmol) in xylene (35 mL) was added anhydrous aluminum chloride (1.93 g, 14.5 mmol) at room temperature. The reaction mixture was then heated at reflux for 1 hour. After being cooled to room temperature, the reaction mixture was slowly poured into ice water with continuous stirring. The resulting solution was extracted with ethyl acetate (50 mL×3). The collected organic layers were then washed with saturated sodium bicarbonate solution and water, dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the crude residue, which was washed with ether to afford 7-chloro-6-fluoro-5-hydroxy-3,4-dihydro-2H-naphthalen-1-one (0.90 g, 89%), which was used in the next step without further purification. MS cald. for C10H8ClFO2 214, obsd. 215 [(M+H)+].

Provenance & Evidence