[OH:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C:8]([NH:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1.O>CC(=O)CC>[C:26]([C:25]1[CH:28]=[CH:29][C:22]([CH2:21][O:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:10][CH3:11])=[O:9])=[CH:12][CH:13]=2)=[CH:23][CH:24]=1)#[N:27]A solution of 500 mg of 2-(4-hydroxy-phenoxy)-N-methyl-acetamide in 25 ml of 2-butanone was treated with 762 mg of potassium carbonate and 595 mg of 4-bromomethyl-benzonitrile. The reaction mixture was stirred at room temperature for 60 h. For the working-up, the reaction mixture was treated with water, then extracted with ethyl acetate. The aqueous layer was re-extracted with ethyl acetate, the combined organic layers were dried over magnesium sulphate and evaporated under reduced pressure. The residue was triturated in ether and the crystals obtained were collected on a filter funnel. After drying there were obtained 744 mg (95% of theory) of 2-[4-(4-cyano-benzyloxy)-phenoxy]-N-methyl-acetamide as white crystals; MS: m/e=297 (M+H)+.
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