Nitric Acid → Carbonic acid 2,3-difluoro-4-methyl-5-nitro-phenyl ester methyl ester

HRID 2065744Notes

Reaction equation

HRID 2065744 reaction equation
[CH3:1][O:2][C:3](=[O:14])[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([F:12])[C:6]=1[F:13].[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:14])[O:4][C:5]1[CH:10]=[C:9]([N+:15]([O-:17])=[O:16])[C:8]([CH3:11])=[C:7]([F:12])[C:6]=1[F:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 59377967Carbonic acid 2,3-difluoro-4-methyl-phenyl ester methyl ester

Product 1

HCID 59377938Carbonic acid 2,3-difluoro-4-methyl-5-nitro-phenyl ester methyl esterYield 49%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of carbonic acid 2,3-difluoro-4-methyl-phenyl ester methyl ester (3.85 g, 19.04 mmol) in sulfuric acid (2.23 ml) at 0° C. was added nitric acid (2.23 ml). The mixture was stirred at 0° C. for one hour. Ice-water was added and the mixture was extracted with dichloromethane. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 95:5) gave 2.3 g (49%) of carbonic acid 2,3-difluoro-4-methyl-5-nitro-phenyl ester methyl ester a clear oil.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification of the crude product by flash chromatography (hexanes:EtOAc 95:5)

Sources & evidence

ORD record
ord-cd467dba63974ed58d3dde0ef8bf29bd
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

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