Ammonium Chloride → 3,4-Difluoroaniline

HRID 730098Notes

Reaction equation

HRID 730098 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+]([O-])=O)[C:3]=1[F:11].[Cl-].[NH4+:13]>CO.O.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:13])=[CH:4][C:3]=1[F:11]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 813351,2-Difluoro-3-nitrobenzene

Product 1

HCID 774693,4-DifluoroanilineYield 43%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Iron powder (28.1 g, 0.502 mol) was added as small portions to 1,2-difluoro nitrobenzene (20.0 g, 0.126 mol) in methanol-(200 ml) and heated to 60° C. Ammonium chloride (48.4 g, 0.91 mol) in water (100 ml) was added drop wise and the reaction mixture refluxed for 5 hr. The reaction mixture was filtered over Celite and washed with methanol. Methanol was removed, and the aqueous layer was extracted with ethylacetate, washed with brine, dried over sodium sulphate and concentrated to yield 1,2-difluoro-4-aminobenzene (7 g, 43%).

Workup

  1. temperaturethe reaction mixture refluxed for 5 hr
  2. filtrationThe reaction mixture was filtered over Celite
  3. washwashed with methanol
  4. customMethanol was removed
  5. extractionthe aqueous layer was extracted with ethylacetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-24cfd4fd62e748e19c24ab8717204924
Source dataset
uspto-grants-2009_09
Patent number
US07582661B2

Reaction notes

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