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

HRID 890743Notes

Reaction equation

HRID 890743 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) δ 7.28 (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-aafc98d81d28441ca3f84d89fa5abc79
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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