Hydrogen Bromide → 1-Bromo-3-isobutylbenzene
Reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7](N)[CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3].N([O-])=O.[Na+].[BrH:16]>>[Br:16][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH:6]=1Participants
4
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 3-isobutylphenylamine (3.80 g) in 48% hydrobromic acid (10 ml) was added aqueous sodium nitrite (2.11 g, 2 ml) below 10° C. over 20 minutes. The reaction mixture was added to a solution of cuprous bromide (7.3 g) in 48% hydrobromic acid (5 ml) at 25° C. After stirred at 25° C. for 1 hour, the mixture was extracted with hexane two times. The extracts were combined, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (150 g) eluting with hexane to give 1-bromo-3-isobutylbenzene (2.61 g) as a colorless oil.