Hydrogen Bromide → 1-Bromo-3-isobutylbenzene

HRID 1034048Notes

Reaction equation

HRID 1034048 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]=1

Participants

4

Reactant 3

HCID 260Hydrogen Bromide2×HCID 190247993-IsobutylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 187549911-Bromo-3-isobutylbenzene

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.

Workup

  1. extractionthe mixture was extracted with hexane two times
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was chromatographed on silica gel (150 g)
  6. washeluting with hexane

Sources & evidence

ORD record
ord-699d5d0ad31d4e5f8c37746571dd7d28
Source dataset
uspto-grants-1994_05
Patent number
US05312829

Reaction notes

Loading…