Water → N-(3,5-difluorophenyl)-3,5-difluoro-2-nitroaniline

HRID 2036613Notes

Reaction equation

HRID 2036613 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[N+:10]([O-:12])=[O:11].[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([F:21])[CH:20]=1)[NH2:17].CC(C)([O-])C.[K+].O>C1COCC1>[F:13][C:14]1[CH:15]=[C:16]([NH:17][C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=2[N+:10]([O-:12])=[O:11])[CH:18]=[C:19]([F:21])[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 675671,3,5-Trifluoro-2-nitrobenzeneHCID 965953,5-DifluoroanilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 67433031N-(3,5-difluorophenyl)-3,5-difluoro-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4,6-trifluoronitrobenzene (1.37 g, 7.74 mmol) and 3,5 difluoroaniline (1 g, 7.74 mmol) in THF (23 mL) was added potassium tert-butoxide (1.3 g, 11.6 mmol) and reaction mixture was stirred at rt for 4 h. After completion of the reaction, water (50 mL) was added and the organic phase extracted with EtOAc (200 mL), dried over sodium sulfate and purified by column chromatography using 100-200 mesh silica gel and 0-10% EtOAc in hexane to provide N-(3,5-difluorophenyl)-3,5-difluoro-2-nitroaniline: LC-MS (ESI) m/z 284.9 [M+H]+.

Workup

  1. additionwas added
  2. extractionthe organic phase extracted with EtOAc (200 mL)
  3. dry with materialdried over sodium sulfate
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-fa3cdb55d7ef48068d5e0b85fd49daf4
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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