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

HRID 473784Notes

Reaction equation

HRID 473784 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-895a08e0b94e49c7bfe687a98cf8c8e9
Source dataset
uspto-grants-2014_01
Patent number
US08637497B2

Reaction notes

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