Benzyl Bromide → HCID 18414640, compound

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][CH3:11])[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([CH2:9][CH2:10][CH3:11])[CH:3]=1

Participants

Procedure

To a 100 ml acetone solution of 4-bromo-2-propylphenol 5.4 g (25.1 mol) and benzyl bromide 5.6 g (32.7 mmol) was added potassium carbonate 5.2 g (37.6 mmol). Resulting suspension was stirred under reflux temperature for overnight. Acetone was removed under reduced pressure, diluted with ethyl acetate and water. Organic phase was separated. Aqueous phase was extracted with ethyl acetate twice. The combined organic phases were dried over anhydrous sodium sulfate, filtered, concentrated, chromatographed on silica gel (hexanes: t-butyl methyl ether) to give 6.96 g of benzyl 4-bromo-2-propylphenyl ether as colorless oil.