Bromoacetonitrile → HCID 22010418, compound

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:32][C:33]#[N:34]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:24])[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH2:32][C:33]#[N:34])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

A stirred solution of 1-(3-benzyloxyphenyl)-2-(2-methylphenyl)ethan-1-one (4 g) in tetrahydrofuran (100 mL) is treated with potassium tert-butoxide (200 mg). After stirring for 30 minutes, it is treated with bromoacetonitrile (0.98 mL), dropwise, and stirring is continued for a further 28 hours. The mixture is then treated with further quantities of potassium tert-butoxide (200 mg) and bromoacetonitrile (0.98 mL) and allowed to stand at room temperature overnight. It is then concentrated under reduced pressure and partitioned between water and ethyl acetate. The organic layer is dried over magnesium sulphate and evaporated, to give a brown oil, which is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (1:9 v/v), to give 1-(3-benzyloxyphenyl)-3-cyano-2-(2-methylphenyl)propan-1-one, in the form of a colourless oil (0.67 g).