Formic Acid → 1-(2-Bromo-4-fluorophenyl)-2,2,2-trifluoroethan-1-amine

HRID 558121Notes

Reaction equation

HRID 558121 reaction equation
[N:1]([CH:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[Br:16])[C:5]([F:8])([F:7])[F:6])=[N+]=[N-].C(O)=O.NN>[Ni].C(O)C>[Br:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[CH:4]([NH2:1])[C:5]([F:6])([F:7])[F:8]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 9321HydrazineHCID 57445068HCID 57445068, compound

Product 1

HCID 513586391-(2-Bromo-4-fluorophenyl)-2,2,2-trifluoroethan-1-amineYield 100.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Add Raney Nickel (1.58 g, 26.8 mmol) to a solution of 1-(1-azido-2,2,2-trifluoro-ethyl)-2-bromo-4-fluoro-benzene (0.8 g, 2.68 mmol), formic acid (1.24 g, 26.8 mmol), and hydrazine (0.86 g, 26.8 mmol) in 10 mL of ethanol. Stir the mixture at RT for 1 h and filter off the excess Nickel. Dilute the mother liquor with water and extract with chloroform. Dry the organic layer over sodium sulfate and concentrate to give the title compound as a brown oil (0.73 g, 100%). MS (ES) m/z 272/274 [M+1]+.

Workup

  1. filtrationfilter off the excess Nickel
  2. additionDilute the mother liquor with water
  3. extractionextract with chloroform
  4. dry with materialDry the organic layer over sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-7aad3f7a12704229ae59c0330403a36c
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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