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

HRID 2406298Notes

Reaction equation

HRID 2406298 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-17d4dcd9a1724c4d89dc35b5a6a0258f
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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