Cesium carbonate → Methyl 3-(difluoromethoxy)-4-nitrobenzoate

HRID 2403469Notes

Reaction equation

HRID 2403469 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([OH:13])[CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:21][CH:22]([F:24])I>CN(C=O)C>[F:21][CH:22]([F:24])[O:13][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[N+:10]([O-:12])=[O:11])[C:3]([O:2][CH3:1])=[O:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 294866Methyl 3-hydroxy-4-nitrobenzoateHCID 2775155Difluoro(iodo)methane

Product 1

HCID 57969921Methyl 3-(difluoromethoxy)-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of 1 g of methyl-3-hydroxy-4-nitrobenzoate, 3.31 g of cesium carbonate in 20 mL of DMF, was carefully added 1.5 equivalents of difluoroiodomethane. The reaction was allowed to warm to room temperature and followed by TLC. Upon completion of the reaction, the mixture was concentrated and purified by silica get chromatography to give 1.2 g of methyl 3-(difluoromethoxy)-4-nitrobenzoate.

Workup

  1. customUpon completion of the reaction
  2. concentrationthe mixture was concentrated
  3. custompurified by silica
  4. customget chromatography

Sources & evidence

ORD record
ord-8a7767169e8b4ac393dc22aa4c5ac46f
Source dataset
uspto-grants-2014_08
Patent number
US08802674B2

Reaction notes

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