Water → N-(2,2-difluoroethyl)-2-nitroaniline

HRID 76358

Reaction equation

HRID 76358 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[F:11][CH:12]([F:15])[CH2:13][NH2:14].O>C(#N)C>[F:11][CH:12]([F:15])[CH2:13][NH:14][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 69451-Chloro-2-nitrobenzeneHCID 1362742,2-Difluoroethanamine

Product 1

HCID 58110950N-(2,2-difluoroethyl)-2-nitroanilineYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2 ml (19 mM) of 2-Chloronitrobenzene and 2.7 ml (36 mM) of 2,2-difluoroethyl amine in 2 ml of acetonitrile were refluxed under stirring for 24 h. Water was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under vacuum to give 3.65 g of N-(2,2-difluoroethyl)-2-nitroaniline as an orange solid. Yield: 95%.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-7d277d5a0c004e918e97e3f25455b131
Source dataset
uspto-grants-2014_09
Patent number
US08835634B2

Linked notes

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