Water → 1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethanol

Participants

Reaction Conditions

Reaction Steps

114.6 ml (57.31 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were taken up at 0° C. in 23 ml of diethyl ether, and 4.95 g (28.65 mmol) of 4′-chloro-2′-fluoroacetophenone dissolved in 5 ml of diethyl ether were slowly added dropwise. Stirring at 0° C. for 1 h was followed by warming to RT, and the reaction solution was mixed with acetonitrile, water and a little kieselguhr, and the mixture was filtered through kieselguhr. The phases of the filtrate were separated and the aqueous phase was extracted twice with diethyl ether. The combined organic phases were washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvents were removed in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient) to result in 4.30 g (70% of theory) of the title compound.

Provenance & Evidence