Acetic Acid → 4-Bromo-2-(propan-2-yl)phenol

HRID 2220604Notes

Reaction equation

HRID 2220604 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].C(O)(=O)C.CS(C)=O.[BrH:19]>O>[Br:19][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 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 69432-Isopropylphenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-isopropylphenol (3.0 g), acetic acid (30 mL) and dimethylsulfoxide (15 mL) was added dropwise 48% hydrobromic acid (15 mL) at room temperature. The mixture was stirred for 30 minutes, poured into water, and extracted with ethyl acetate. The organic layer was washed successively with water, a saturated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (4.62 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7dc8c2fec4f0426489a9ebc4e7d555c2
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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