5-Bromopentanenitrile → 4-(2-Propyl-3-chlorophenoxy)butane nitrile
Reaction equation
[CH2:1]([C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11])[CH2:2][CH3:3].BrC[CH2:14][CH2:15][CH2:16][C:17]#[N:18]>>[CH2:1]([C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH2:14][CH2:15][CH2:16][C:17]#[N:18])[CH2:2][CH3:3]Participants
3
Procedure
Five and seven-tenths grams of 2-propyl3-chlorophenol were then reacted with 5.9 ml. of 5bromovaleronitrile following the procedure of Example 2A. The resulting 4-(2-propyl-3-chlorophenoxy)butane nitrile was provided by chromatography. This purified nitrile intermediate (3.3 g.) was dissolved in about 65 ml. of methylene chloride to which 3.0 g. of aluminum chloride and 1.7 ml. of acetyl chloride had been added and the reaction was heated to reflux overnight. The reaction was cooled, additional methylene chloride was added, and the mixture was poured into ice/hydrochloric acid. The layers were separated and the organic layer was washed first with an aqueous sodium bicarbonate solution and then with water. The organic solution was dried over sodium sulfate and evaporated to dryness. Purification by chromatography provided 2.67 g. of the desired 4-(2-propyl-3-chloro4-acetylphenoxy)butane nitrile. NMR.