Diethyl Ether → HCID 86683005, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-5-chloro-benzonitrile (1 g, 6.55 mmol) in diethyl ether (20 ml) was added 3-isopropyl phenyl magnesium bromide (prepared freshly as a 1M solution in diethyl ether; 20 ml, 19.66 mmol) drop wise at 0° C., and the resulting reaction mixture was stirred for 1 h under reflux conditions followed by another 16 h at room temperature. The reaction mixture was cooled to 5° C., quenched with water followed by 2N aqueous HCl solution. The reaction mixture was then stirred at 45° C. for an additional 5 h. The reaction mixture was made basic (pH 8-9) with aqueous solution of NaOH, and then extracted with diethyl ether (2×30 ml). The organic phases were combined and washed with brine (25 ml), dried over anhydrous Na2SO4, concentrated in vacuo to give a crude residue which was purified by flash column chromatography (5% EtOAc in hexane) to afford (2-amino-5-chloro-phenyl)-(3-isopropyl-phenyl)-methanone (1.1 g, 61%) as a yellow sticky liquid. LC-MS (ESI): 274 (M+H)+.

Provenance & Evidence