O-Cresol → 4-Bromo-2-methylphenol

HRID 1978746Notes

Reaction equation

HRID 1978746 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:9].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.CO>[Br:9][C:3]1[CH:4]=[CH:5][C:6]([OH:7])=[C:1]([CH3:8])[CH:2]=1

Participants

5

Reactant 2

HCID 335O-CresolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 168964-Bromo-2-methylphenolYield 178.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of o-cresol (6.0 g) in dichloromethane (120 ml) and methanol (80 ml) was added little by little the solid of tetrabutylammonium tribromide (27.0 g), and the mixture was stirred for 1 hour and concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ether (4 times). The organic layer was washed with saturated brine (twice) and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give solid, which was dried in vacuo to give colorless solid of 4-bromo-2-methylphenol (9.3 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added water
  3. extractionthe mixture was extracted with ether (4 times)
  4. washThe organic layer was washed with saturated brine (twice) and
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customto give solid, which
  8. customwas dried in vacuo

Sources & evidence

ORD record
ord-ed288133ea38426ab530bfb9101ade3c
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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