2-Chloro-4-fluorobenzaldehyde → 1-(2-Chloro-4-fluorophenyl)ethan-1-ol

Temperature

0 °C

A solution of 5.25 g (0.033 mole) of 2-chloro-4-fluorobenzaldehyde in 100 ml of diethyl ether was cooled to -10° C., and 11.2 ml (0.033 mole) of a 2.95M solution of methylmagnesium bromide in diethyl ether was added dropwise with stirring. The reaction mixture was warmed to 0° C. and was stirred for several hours. After warming to room temperature, the reaction mixture was poured into an ice/water mixture. The resulting mixture was extracted with methylene chloride. The solvent was evaporated from the extract under reduced pressure, and the residue was passed through a column of silica gel, eluting first with heptane and then with ethyl acetate/heptane (1/9). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure, leaving 1.46 g of 1-(2-chloro-4-fluorophenyl)ethanol as an amber oil. The nmr and ir spectra were consistent with the proposed structure. This reaction was repeated on a larger scale to provide sufficient 1-(2-chloro-4-fluorophenyl)ethanol for Step D.

1. stirringwas stirred for several hours
2. temperatureAfter warming to room temperature
3. extractionThe resulting mixture was extracted with methylene chloride
4. customThe solvent was evaporated from the
5. extractionextract under reduced pressure
6. washeluting first with heptane
7. customthe solvent was evaporated under reduced pressure

ORD record

ord-6b96c2ad762747f781ae2debeaab9828

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04846882