[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:23][CH2:24][CH2:25][C:26]#[N:27]>O>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:23][CH2:24][CH2:25][C:26]#[N:27]A suspension of 3-dimethylaminophenol (5 g), potassium carbonate (10.05 g) and dimethylformamide (85 ml) was stirred at room temperature for 5 hours. 4-Bromobutyronitrile (7.3 ml) was added and the suspension stirred for 17 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extracts were washed with water, dried and the solvent removed to yield 4-(3-dimethylaminophenoxy)butyronitrile.
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