Diethyl Ether → (2-Amino-5-chlorophenyl)(3-chlorophenyl)methanone

Participants

Reaction Conditions

Reaction Steps

To the stirred solution of 2-amino-5-chloro-benzonitrile (500 mg, 3.28 mmol) in diethyl ether (10 ml) was added 3-chloro phenyl magnesium bromide (freshly prepared 1M solution in ether, 10 ml, 9.83 mmol) drop wise at 0° C. and the resulting reaction mixture was refluxed for 1 h. Then the mixture was stirred for 16 h at 25° C., cooled to 5° C. and quenched with water followed by 2 N HCl solution (20 ml). The reaction mixture was stirred at 45° C. for 5 h and then the pH of the reaction mixture was adjusted to 8-9 with 2N aqueous NaOH solution. The mixture was extracted with diethyl ether (3×30 ml) and the combined organic extracts were washed with brine (25 ml), dried over sodium sulfate and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (5% ethyl acetate in hexane) to yield (2-amino-5-chloro-phenyl)-(3-chloro-phenyl)-methanone (550 mg, 63%) as a yellow solid. LC-MS (ESI): 266 (M+H)+.

Provenance & Evidence