Methyl iodide → 4-Bromo-2-fluoroanisole

HRID 2078409Notes

Reaction equation

HRID 2078409 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-fluoroanisole

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; see step (i) above) and K2CO3 (303.92 g, 2.19 mol) in dry acetone (1.7 L). Stirring was continued at 60° C. for two days under a nitrogen atmosphere before the reaction mixture was filtered and the solvent was concentrated under reduced pressure. This provided 4-bromo-2-fluoro-1-methoxybenzene (225 g) as a liquid, which was employed directly in the next step without further purification.

Workup

  1. stirringStirring
  2. filtrationwas filtered
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThis provided 4-bromo-2-fluoro-1-methoxybenzene (225 g) as a liquid, which was employed directly in the next step without further purification

Sources & evidence

ORD record
ord-c09b58ba7ab14fd7bbf720dcc157167a
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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