Water → 2-Bromo-5-fluoroanisole

HRID 1502021Notes

Reaction equation

HRID 1502021 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[C:10]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 70180432-Bromo-5-fluoroanisole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-5-fluorophenol (15 g, 79 mmol) in 125 mL of anhydrous DMF was added K2CO3 (17.0 g, 138 mmol) and MeI (14.0 g, 102 mmol) under cooling, then the reaction was stirred at room temperature for 3 hours. The mixture was poured to water, extracted with diethyl ether, washed with water and brine, dried over anhydrous Na2SO4 and concentrated to give 1-bromo-4-fluoro-2-methoxybenzene.

Workup

  1. temperatureunder cooling
  2. extractionextracted with diethyl ether
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e9151a21558b4905b9b7fd7244f9b89c
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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