5-Chloro-2-fluorobenzaldehyde → 1-(5-Chloro-2-fluorophenyl)propan-1-ol

Temperature

0 °C

To a solution of 5-chloro-2-fluorobenzaldehyde (1 g, 6.3 mmol) in diethyl ether (20 mL) cooled at −78° C. was added a solution of 3.0M ethylmagnesium bromide in ether (4.2 mL, 13 mmol) dropwise over 5 minutes. The reaction mixture was warmed to 0° C. and after 30 minutes was quenched with a few drops of saturated aqueous ammonium chloride solution. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 4 g, ISCO, 0-30% ethyl acetate in heptane) to afford the title compound as a pale yellow oil (850 mg, 71%), which was used in the next step without further purification.

1. customwas quenched with a few drops of saturated aqueous ammonium chloride solution
2. additionThe reaction mixture was diluted with ethyl acetate (50 mL)
3. washwashed with water (50 mL)
4. customThe organic layer was separated
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. customto afford a residue that
9. customwas purified by flash chromatography (silica, 4 g, ISCO, 0-30% ethyl acetate in heptane)

ORD record

ord-82ed36c19e184ef5b4953eb98e9ce4b2

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206175B2