3-Chloro-2-fluoro-6-(trifluoromethyl)benzaldehyde → HCID 86721087, compound

Participants

Reaction Steps

To a solution of 3-chloro-2-fluoro-6-(trifluoromethyl)benzaldehyde (2.052 g, 9.06 mmol) in THF (30 mL) under nitrogen at −78° C. was added dropwise vinyl magnesium bromide (1 M in THF) (11.77 mL, 11.77 mmol). The mixture was stirred for 15 minutes at this temperature then the cooling bath was removed allowing the solution to warm to ambient temperature where it was stirred for 1 h. The reaction was cooled to 0° C. and quenched with 20 mL of aqueous NH4Cl (saturated) and the solvent was removed under a stream of nitrogen. The solid residue was taken up in water/ethyl acetate and phases were separated. The aqueous layer was extracted twice with ethyl acetate and the combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to give an oil. The oil was then purified using silica gel chromatography. The desired fractions were combined together to give 1-(3-chloro-2-fluoro-6-(trifluoromethyl)phenyl)prop-2-en-1-ol (1.322 g, 57%) as a faint yellow colored oil.

Provenance & Evidence