2-Isopropylphenol → 4-Bromo-2-(propan-2-yl)phenol

HRID 260786Notes

Reaction equation

HRID 260786 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].[Br-:11].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:11][C:8]1[CH:7]=[CH:6][C:5]([OH:10])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=1

Participants

5

Reactant 3

HCID 69432-IsopropylphenolHCID 24437Sodium SulfiteHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 147934824-Bromo-2-(propan-2-yl)phenolYield 179.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

First, 20.4 g of 2-isopropylphenol and 750 ml of chloroform were charged into a reaction vessel, and 80 g of tetra-n-butylammonium tribromide was added at room temperature (about 20° C.) with stirring and the mixture was stirred at room temperature for additional 24 hours. To the reaction solution, 750 ml of a saturated sodium sulfite solution was added, and the mixture was shaken vigorously to concentrate the chloroform layer. To the residue, 500 ml of diethyl ether and 500 ml of 10% hydrochloric acid were added, and the mixture was shaken vigorously. The ether layer was dried over anhydrous magnesium sulfate and concentrated to give 32 g of 4-bromo-2-isopropylphenol (yield, 100%).

Workup

  1. stirringthe mixture was stirred at room temperature for additional 24 hours
  2. stirringthe mixture was shaken vigorously
  3. concentrationto concentrate the chloroform layer
  4. additionTo the residue, 500 ml of diethyl ether and 500 ml of 10% hydrochloric acid were added
  5. stirringthe mixture was shaken vigorously
  6. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c2ed92e29dd94293a8403662381d075b
Source dataset
uspto-grants-1996_06
Patent number
US05530015

Reaction notes

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