Hydrogen Bromide → 1-(Bromomethyl)-4-(2-methylpropyl)benzene

HRID 1699007Notes

Reaction equation

HRID 1699007 reaction equation
[BrH:1].[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=1)[CH:3]([CH3:5])[CH3:4]>CCOCC>[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Br:1])=[CH:8][CH:7]=1)[CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14620446[4-(2-Methylpropyl)phenyl]methanol

Product 1

HCID 146204471-(Bromomethyl)-4-(2-methylpropyl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

HBr gas was bubbled through a solution of (4-isobutyl-phenyl)-methanol (5 g, 28 mmol) in Et2O (50 mL) for 10-15 minutes. The reaction was stirred for 1 h and was poured onto ice (100 g). Et2O was added and the organic solution was washed with brine (2×). The organic solution was dried (MgSO4), filtered, and concentrated to provide the title compound (6 g). 1H NMR (400 MHz, CDCl3) δ7.28 (d, 2H), 7.10 (d, 2H), 4.49 (s, 2H), 2.45 (d, 2H), 1.84 (m, 1H), 0.89 (d, 6H).

Workup

  1. additionwas poured onto ice (100 g)
  2. washthe organic solution was washed with brine (2×)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-64d1464bc70f4693a96514d804ef5629
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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