1,2,4-Trifluoro-5-nitrobenzene → 1,4-Difluoro-2-methoxy-5-nitrobenzene

HRID 493126Notes

Reaction equation

HRID 493126 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1F.[CH3:13][O-:14].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[O:14][CH3:13]

Participants

5

Reactant 2

HCID 750121,2,4-Trifluoro-5-nitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 217306651,4-Difluoro-2-methoxy-5-nitrobenzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

1,2,4-Trifluoro-5-nitrobenzene (10 g, 56.5 mmol) was dissolved in methanol, cooled in ice and treated with 25% sodium methoxide in methanol. After being stirred at room temperature for 6 hours the mixture was diluted with water and extracted with ethyl acetate to give 1,4-difluoro-2-methoxy-5-nitrobenzene (10.1 g). This was dissolved in ethanol (400 ml) and hydrogenated over 10% palladium on carbon to give the title compound (7.8 g).

Workup

  1. temperaturecooled in ice
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-ea2efaa323624e54b7d65cc41764e43e
Source dataset
uspto-grants-2009_05
Patent number
US07534793B2

Reaction notes

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