Stannous chloride dihydrate → 4-Chloro-2,5-difluoroaniline

HRID 1988533Notes

Reaction equation

HRID 1988533 reaction equation
O.O.[Sn](Cl)Cl.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([N+:14]([O-])=O)=[CH:9][C:8]=1[F:17].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:6][C:7]1[C:8]([F:17])=[CH:9][C:10]([NH2:14])=[C:11]([F:13])[CH:12]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 157514831-Chloro-2,5-difluoro-4-nitrobenzene

Product 1

HCID 146245254-Chloro-2,5-difluoroanilineYield 73.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Tin (II) chloride dihydrate (15.5 g, 68.7 mmol) was dissolved in ethyl acetate (50 mL) and 1-chloro-2,5-difluoro-4-nitrobenzene (2.65 g, 13.7 mmol) was added dropwise. The reaction mixture was then stirred at 70° C. for 1 h. The reaction mixture was then carefully added to saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. The organic phase was washed several more times with water, dried, filtered, concentrated and purified by flash chromatography on silica gel (hexane/diethyl ether) to give the title compound as a white solid (1.65 g, 73.9% yield): 1H NMR (CDCl3): δ 7.02 (dd, 1H), 6.57 (dd, 1H), 3.81 (br s, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed several more times with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (hexane/diethyl ether)

Sources & evidence

ORD record
ord-7ac5aa8571dd470a8381c5ed0f67aaba
Source dataset
uspto-grants-2010_01
Patent number
US07642220B2

Reaction notes

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