p-Bromochlorobenzene → (4-Chlorophenyl)(4-cyanophenyl)methanol

Participants

Reaction Steps

0.67 g (27.42 mmol) of magnesium turnings were dried by heating under argon and, after cooling to RT, 30 ml of tetrahydrofuran and 2 ml of dibromoethane were added. At 0° C., 5.00 g (26.12 mmol) of 4-chlorobromobenzene in 30 ml of tetrahydrofuran were slowly added to the mixture, and the mixture was stirred at RT for 30 min. Addition of 3.77 g (28.73 mmol) of 4-cyanobenzaldehyde in 30 ml of tetrahydrofuran was followed by stirring for 3 h. The THF was removed from the reaction solution in a rotary evaporator, and the residue was taken up in dichloromethane. It was washed with 1N hydrochloric acid, dried over sodium sulfate and filtered, and the solvents were removed in vacuo. The precipitate which separated out of the oily residue was filtered off, washed with diethyl ether and then purified by preparative HPLC (mobile phase: acetonitrile/water gradient). Acetonitrile was removed from the product-containing fractions in a rotary evaporator, and the aqueous residue was extracted with dichloromethane. Removal of the solvent resulted in 1.43 g (23% of theory) of the title compound.

Provenance & Evidence