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

HRID 2078402Notes

Reaction equation

HRID 2078402 reaction equation
CI.[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+]>CC(C)=O>[CH3:13][O:11][C:7]1[C:8]([F:10])=[CH:9][C:4]([Br:3])=[CH:5][C:6]=1[F:12]

Participants

5

Reactant 3

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

Product 1

HCID 27732874-Bromo-2,6-difluoroanisoleYield 51.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl iodide (17.11 g, 0.12 mol) was added at 0° C. to a well stirred suspension of 4-bromo-2,6-difluorophenol (21 g, 0.1 mol; see step (i) above) and K2CO3 (27.78 g, 0.2 mol) in dry acetone (150 mL). Stirring was continued at 60° C. overnight under a nitrogen atmosphere. The reaction mixture was filtered, the solvent was evaporated and the residue was purified by column chromatography over silica gel, using petroleum ether as eluent, to give 11.5 g of the sub-title compound as a colourless liquid.

Workup

  1. stirringStirring
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was evaporated
  4. customthe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-88435cb1459347d6aaf95c7884881185
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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