Water → 1,5-Difluoro-3-methoxy-2-nitrobenzene

HRID 1372564Notes

Reaction equation

HRID 1372564 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.O.[F:10][C:11]1[C:12]([N+:19]([O-:21])=[O:20])=[C:13](O)[CH:14]=[C:15]([F:17])[CH:16]=1>CN(C=O)C>[F:10][C:11]1[C:12]([N+:19]([O-:21])=[O:20])=[C:13]([O:4][CH3:1])[CH:14]=[C:15]([F:17])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118195353,5-Difluoro-2-nitrophenol

Product 1

HCID 103301291,5-Difluoro-3-methoxy-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (50 ml) was dissolved 3,5-difluoro-2-nitrophenol. Potassium carbonate (10.4 g, 75.5 mmol) and methyl iodide (6.3 ml, 100.6 mmol) were added and the mixture was stirred for 15 hours at room temperature. Water (300 ml) was added, followed by extraction with ether (500 ml). The extract was washed with saturated brine (2×200 ml), dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (8.29 g, 87%) was obtained as a yellow crystalline powder.

Workup

  1. extractionfollowed by extraction with ether (500 ml)
  2. washThe extract was washed with saturated brine (2×200 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent, whereby the title compound (8.29 g, 87%)
  6. customwas obtained as a yellow crystalline powder

Sources & evidence

ORD record
ord-56ec8e648bb043bfaa792155fa2359e2
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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