Hydrogen Bromide → 4-Bromo-2-(propan-2-yl)phenol

HRID 1664629Notes

Reaction equation

HRID 1664629 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].[BrH:11].CS(C)=O>C(O)(=O)C.O>[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

6

Reactant 3

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 69432-Isopropylphenol

Product 1

HCID 147934824-Bromo-2-(propan-2-yl)phenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-isopropylphenol (2.0 g) in acetic acid (20 mL) was added hydrobromic acid (48%, 10 mL) followed by dropwise addition of DMSO (10 mL). The mixture was stirred another 20 min and diluted with water, extracted with diethyl ether. The combined extract was washed with saturated NaHCO3, water, brine, dried and concentrated to give the product 4-bromo-2-isopropylphenol (2.2 g, HPLC purity 95%).

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe combined extract
  3. washwas washed with saturated NaHCO3, water, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-910022ebb571409cb79caea484c7f024
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Reaction notes

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