Methyl iodide → 4-Bromo-2,6-difluoroanisole

HRID 746770

Reaction equation

HRID 746770 reaction equation
IC.[Br:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[C:6]([F:12])[CH:5]=1.[C:13](=O)([O-])[O-].[K+].[K+].ClCCl>CC(C)=O>[Br:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH3:13])=[C:6]([F:12])[CH:5]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27362924-Bromo-2,6-difluorophenol

Product 1

HCID 27732874-Bromo-2,6-difluoroanisole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Add iodomethane (2.0 ml, 32.1 mmol) dropwise to a suspension of 4-bromo-2,6-difluorophenol (5.90 g, 28.2 mmol) and potassium carbonate (4.40 g, 31.8 mmol) in acetone (50 ml) at room temperature while stirring vigorously. Heat the mixture under reflux overnight. Evaporate acetone and add dichloromethane. Filter through silica eluting the product with dichloromethane/EtOAc. Concentrate to yield the title compound.

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux overnight
  3. filtrationFilter through silica eluting the product with dichloromethane/EtOAc
  4. concentrationConcentrate

Sources & evidence

ORD record
ord-a291ed1aa0994e328206e6d5aeacc4dc
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Linked notes

Loading…