Methanol → 3-Chloro-5-hydroxy-N,N-diisopropyl-benzamide

To a stirred solution of 3-chloro-N,N-diisopropyl-5-methoxy-benzamide (2.96 g) in anhydrous dichloromethane (30 ml) at −78° C. was added boron tribromide solution in dichloromethane (40 ml). The reaction mixture was allowed to warm to ambient temperature and stirred for 19 h. The reaction mixture was cooled to −78° C. and methanol (20 ml) added. The reaction mixture was allowed to warm back to ambient temperature, stirred for 24 h, and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with water and dried with brine and over sodium sulphate. The crude product was purified by flash column chromatography, eluting with cyclohexane:ethyl acetate (1:1), to give the title compound as a white solid (2.24 g).

1. temperatureThe reaction mixture was cooled to −78° C.
2. temperatureto warm back to ambient temperature
3. stirringstirred for 24 h
4. concentrationconcentrated under reduced pressure
5. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
6. washThe organic phase was washed with water
7. dry with materialdried with brine and over sodium sulphate
8. customThe crude product was purified by flash column chromatography
9. washeluting with cyclohexane:ethyl acetate (1:1)

ORD record

ord-4726744de30e480e8da3315a1901b922

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06670381B2