Dimethylformamide → 4-(2-oxo-2-phenylethyl)benzonitrile

Participants

Reaction Steps

The 2-(4-cyanophenyl)-1-phenylethanone was synthesized from 4-cyanobenzyl bromide and ω-cyano-N,N-diethylbenzenemethanamine: 3.95 g (0.16 mol) of sodium hydride was suspended in 80 mL of DMF under nitrogen and 29.9 g (0.16 mol) of the methanamine in 20 mL of DMF was added dropwise. When evolution of hydrogen had ceased, 31.2 g (0.16 mol) of the benzyl bromide in 30 mL of toluene was added and the reaction stirred 3 hr at room temperature. The reaction was stripped, 300 mL of 6N HCL was added and the suspension was stirred 4 hr, let sit 18 hr and extracted with chloroform. The chloroform extract was stripped, dissolved in ethyl acetate, and filtered through silica gel to remove a purple impurity. The ethyl acetate solution was stripped, the residue was triturated in ether and recrystallized from methanol to give 7.72 g of 2-(4-cyanophenyl)-1-phenylethanone, mp 113°-114° C.

Provenance & Evidence