Dimethyl Sulfate → 1-Bromo-2-fluoro-4-methoxybenzene

HRID 216336Notes

Reaction equation

HRID 216336 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[C:10]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:10])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 37184441-Bromo-2-fluoro-4-methoxybenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 1-bromo-2-fluoro-4-hydroxybenzene (100 g, 0.52 mol) and K2CO3 (179.4 g, 1.3 mol) in 1300 mL acetone was added dimethyl sulfate (98.38 g, 0.78 mol). After refluxing overnight, the reaction mixture was cooled, filtered and dried over Na2SO4, and the filtrate was concentrated to afford 1-bromo-2-fluoro-4-methoxybenzene as a brown oil.

Workup

  1. temperatureAfter refluxing overnight
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. dry with materialdried over Na2SO4
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1bb0054a91a148f091fae3899c7b253f
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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