Methane → 4-Chloro-2-fluoro-5-(2,2-difluorocyclopropylmethoxy)aniline

HRID 1722922Notes

Reaction equation

HRID 1722922 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:12][C:11]2([F:14])[F:13])=[CH:6][C:5]([N+:15]([O-])=O)=[C:4]([F:18])[CH:3]=1.C.[H][H]>C(O)C.[Pd]>[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:12][C:11]2([F:13])[F:14])=[CH:6][C:5]([NH2:15])=[C:4]([F:18])[CH:3]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 141294314-Chloro-2-fluoro-5-(2,2-difluorocyclopropylmethoxy)nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 141294324-Chloro-2-fluoro-5-(2,2-difluorocyclopropylmethoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

36.9 g 4-Chloro-2-fluoro-5-(2,2-difluorocyclopropylmethoxy)nitrobenzene in 600 ml ethanol was hydrogenated by the addition of 5 g of 10% palladium metal on activated charcoal at room temperature and normal pressure. After the uptake of hydrogen is complete the catalyst is filtered off, the solvent evaporated to give 29.3 g(=89% of theory) of an oil, whose nmr spectrum is as follows: δ=1.1-2.2 ppm (m) 3H, δ=4.0 ppm (d 10 Hz wide) 2H, δ=5 ppm (s wide) 2H, δ=6.5 ppm (d 7 Hz) 1H, δ=7.0 ppm (d 10 Hz) 1H.

Workup

  1. customat room temperature
  2. filtrationis filtered off
  3. customthe solvent evaporated
  4. customto give 29.3 g(=89% of theory) of an oil, whose nmr spectrum

Sources & evidence

ORD record
ord-d4b1d39ca17d4736af2c4dc68246cee3
Source dataset
uspto-grants-1989_08
Patent number
US04859230

Reaction notes

Loading…