Trifluoroacetic acid → Ethyl 2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzoate

HRID 1410216Notes

Reaction equation

HRID 1410216 reaction equation
[F:1][CH:2]([F:5])[CH2:3][OH:4].F[C:7]1[CH:17]=[C:16]([NH:18][CH3:19])[C:15]([N+:20]([O-:22])=[O:21])=[CH:14][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[H-].[Na+].C(O)(C(F)(F)F)=O>C1COCC1.CN(C=O)C>[F:1][CH:2]([F:5])[CH2:3][O:4][C:7]1[CH:17]=[C:16]([NH:18][CH3:19])[C:15]([N+:20]([O-:22])=[O:21])=[CH:14][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24758Sodium hydrideHCID 1361872,2-Difluoroethan-1-olHCID 59529818HCID 59529818, compound

Product 1

HCID 59529798Ethyl 2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2-difluoroethanol (1.7 g; 20.6 mmol) in THF (50 mL) was added to a solution of ethyl 2-fluoro-4-(methylamino)-5-nitrobenzoate (5.0 g; 20.6 mmol) in DMF (100 mL). Sodium hydride (0.824 g; 60%; 20.6 mmol) was added in portions and the mixture was stirred over night at rt. A solution of TFA (30 mL; 0.45 M aq) was added and the mixture was concentrated. The resulting precipitation was filtered off, washed with water, dried and recrystallized from EtOH/water to give the sub-title compound. Yield: 4.8 g (76%).

Workup

  1. concentrationthe mixture was concentrated
  2. customThe resulting precipitation
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried
  6. customrecrystallized from EtOH/water

Sources & evidence

ORD record
ord-584964a19807459284afe968b008e6c3
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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