Hydrogen Bromide → 4-Butylbenzyl Bromide
Reaction equation
[BrH:1].[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5]>C(Cl)Cl>[Br:1][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:2][CH2:3][CH2:4][CH3:5])=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
HBr was bubbled into a solution of (4-butyl-phenyl)-methanol (10.0 g, 60.9 mmol) in CH2Cl2 (100 mL) for 15 minutes. The reaction was stirred for an additional 45 minutes and was poured onto ice water. The aqueous solution was extracted with CH2Cl2 (2×) and was dried (MgSO4), filtered, and concentrated to provide the title compound which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.29 (d, 2H), 7.14 (d, 2H), 4.49 (s, 2H), 2.60 (t, 2H), 1.58 (m, 2H), 1.36 (m, 2H), 0.92 (t, 3H).
Workup
- additionwas poured onto ice water
- extractionThe aqueous solution was extracted with CH2Cl2 (2×)
- dry with materialwas dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0baac2a3b58946099edef871f492e969
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06998423B2
Reaction notes
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