Hydrogen Bromide → 4-Butylbenzyl Bromide

HRID 480282Notes

Reaction equation

HRID 480282 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]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 5782884-Butylbenzyl alcohol

Product 1

HCID 121508404-Butylbenzyl Bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. additionwas poured onto ice water
  2. extractionThe aqueous solution was extracted with CH2Cl2 (2×)
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8239addee80f46c9939124f781be2ddf
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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