Hydrogen Bromide → 1-(1-Bromo-2-methylpropyl)-4-chlorobenzene

HRID 1977719Notes

Reaction equation

HRID 1977719 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6](O)[CH:7]([CH3:9])[CH3:8])=[CH:4][CH:3]=1.[BrH:13]>>[Br:13][CH:6]([C:5]1[CH:11]=[CH:12][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:7]([CH3:9])[CH3:8]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 202426Benzenemethanol, 4-chloro-alpha-(1-methylethyl)-

Product 1

HCID 217034861-(1-Bromo-2-methylpropyl)-4-chlorobenzene

Procedure

A mixture of p-chloro-α-isopropylbenzyl alcohol (33.08 g) in 48% hydrobromic acid (330 mL) is stirred at room temperature for 1 hour and extracted with hexanes. The combined organic extracts are washed sequentially with water, saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a yellow oil (42.98 g) which is identified by NMR spectral analysis.

Workup

  1. extractionextracted with hexanes
  2. washThe combined organic extracts are washed sequentially with water, saturated sodium hydrogen carbonate solution and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ade00b8df7ff44f3a12cdf2e2885c98d
Source dataset
uspto-grants-2001_05
Patent number
US06235754B1

Reaction notes

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