2-Bromophenol → 1-Bromo-2-(2-methylpropoxy)benzene

HRID 1289178Notes

Reaction equation

HRID 1289178 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([O-])([O-])=O.[K+].[K+].I[CH2:16][CH:17]([CH3:19])[CH3:18]>CC(C)=O>[CH2:16]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 10556Isobutyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 189257731-Bromo-2-(2-methylpropoxy)benzeneYield 25%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-bromophenol (0.67 ml, 5.8 mmol) in 25 ml acetone was added K2CO3 (2.0 g, 14.5 mmol) and 1-iodo-2-methylpropane (0.75 ml, 6.4 mmol). The reaction mixture was heated to reflux for 19 h, cooled to ambient temperature and filtered. The solvent was removed under reduced pressure and the residue was taken up in EtOAc. The organic phase was washed with 1N NaOH×2, water and brine. Drying over Na2 SO4 afforded 330 mg (25%) of 2-isobutoxybromobenzene.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 19 h
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. washThe organic phase was washed with 1N NaOH×2, water and brine
  6. customDrying over Na2 SO4

Sources & evidence

ORD record
ord-1a858d066ef94350b5e480fb11b0bdcb
Source dataset
uspto-grants-1998_05
Patent number
US05747540

Reaction notes

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