Aluminum(III) Chloride → HCID 59192513, compound

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)+].

1. temperatureThe reaction mixture was then heated
2. temperatureat reflux for 1 hour
3. extractionThe resulting solution was extracted with ethyl acetate (50 mL×3)
4. washThe collected organic layers were then washed with saturated sodium bicarbonate solution and water
5. dry with materialdried with anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give the crude residue, which
9. washwas washed with ether

ORD record

ord-48f61cdafa994b42a7f8ca6ea85a9aac

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263656B2