5-Bromo-2-fluorobenzaldehyde → (5-Bromo-2-fluorophenyl)(4-chlorophenyl)methanol

A solution of 5-bromo-2-fluorobenzaldehyde (10.2 g, 50 mmol) in anhydrous tetrahydrofuran (200 mL) was cooled to −78° C. A solution of 4-chlorophenyl-magnesium bromide (1M in diethyl ether, 60 mL, 60 mmol) was added via syringe over 8 minutes. Stirring was continued at low temperature for 5 minutes and the reaction was warmed up to room temperature and stirred for 1 hour at this temperature. The solution was cooled in an ice-water bath and quenched by addition of saturated aqueous ammonium chloride solution (40 mL). The organic phase was decanted and the aqueous residue was concentrated under reduced pressure to remove any remaining organic solvent. The aqueous phase was extracted with ethyl acetate (200 mL×2) and the extracts were combined with the decanted tetrahydrofuran solution. This solution was washed with brine (25 mL) and was dried (sodium sulfate), filtered and concentrated under reduced pressure, giving crude (5-bromo-2-fluorophenyl)-(4-chlorophenyl)-methanol (15.2 g, 96% yield) as a yellow solid.

1. stirringstirred for 1 hour at this temperature
2. temperatureThe solution was cooled in an ice-water bath
3. customquenched by addition of saturated aqueous ammonium chloride solution (40 mL)
4. customThe organic phase was decanted
5. concentrationthe aqueous residue was concentrated under reduced pressure
6. customto remove any remaining organic solvent
7. extractionThe aqueous phase was extracted with ethyl acetate (200 mL×2)
8. washThis solution was washed with brine (25 mL)
9. dry with materialwas dried (sodium sulfate)
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD 기록

ord-51573e1755fb4bda914816c524443ed7

출처 데이터셋

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08080580B2