Methyl iodide → 4-Bromo-2-fluoroanisole

HRID 1992362Notes

Reaction equation

HRID 1992362 reaction equation
CI.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1.[C:12]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:12])=[C:6]([F:11])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 753784-Bromo-2-fluoroanisoleYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl iodide (182.1 ml, 1.319 mol) was added at 0° C. to a well stirred suspension of 4-bromo-2-fluorophenol (210 g, 1.099 mol, from step (i) above ) and K2CO3 (303.92 g, 2.19 mol) in dry acetone (1.7 L) and stirring continued at 60° C. for two days under nitrogen atmosphere. The reaction mixture was filtered and the solvent was concentrated under reduced pressure to yield 4-bromo-2-fluoro-anisole (225 g) as a liquid. This was directly taken for next step without further purification.

Workup

  1. stirringstirring
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f12b6b3ba1dd4fc6b71558bfe2f60331
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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