Potassium Carbonate → 2,3-Difluoro-1-methyl-4-nitrobenzene

HRID 447769Notes

Reaction equation

HRID 447769 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[CH2:12]C(O)=O.FC1C(F)=CC=C([N+]([O-])=O)C=1CC(O)=O.C(=O)([O-])[O-].[K+].[K+].FC1C(F)=CC=C([N+]([O-])=O)C=1C>CN(C)C=O>[F:1][C:2]1[C:7]([F:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[CH3:12]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 22475350(2,3-Difluoro-6-nitrophenyl)acetic acidHCID 469413031,2-Difluoro-3-methyl-4-nitrobenzeneHCID 53411782HCID 53411782, compound

Product 1

HCID 587852252,3-Difluoro-1-methyl-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of 2,3-difluoro-4-nitrophenylacetic acid and 2,3-difluoro-6-nitrophenylacetic acid from D16 (13.5 g) was dissolved in dimethylformamide (100 ml) and potassium carbonate (8.5 g) added. After stirring at 50° C. for 30 min the cooled solution was partitioned between aqueous hydrochloric acid and hexane. Drying (MgSO4), evaporation, and chromatography (0-5% ethyl acetate in hexane, 70 g silica column) gave 3.2 g of a 3:1 mixture of the title compound and 2,3-difluoro-6-nitrotoluene.

Workup

  1. customwas partitioned between aqueous hydrochloric acid and hexane
  2. customDrying
  3. custom(MgSO4), evaporation, and chromatography (0-5% ethyl acetate in hexane, 70 g silica column)
  4. customgave

Sources & evidence

ORD record
ord-29e16d5b73044fad9e91932972fb2228
Source dataset
uspto-grants-2013_07
Patent number
US08481566B2

Reaction notes

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