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

HRID 30735

Reaction equation

HRID 30735 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 min, and poured into water. The resulting mixture was 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. extractionThe resulting mixture was extracted 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-db39999e8b964026813c5b0fa100f377
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Linked notes

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