Reaction #2075715

Reaction equation

Tin (II) chloride dihydrate

1-chloro-2,5-difluoro-4-nitrobenzene

sodium bicarbonate

→

title compound

Yield 73.9%

4-Chloro-2,5-difluorophenylamine

Yield 73.9%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe organic phase was washed several more times with water
3. 3
   Otherdried
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   Otherpurified by flash chromatography on silica gel (hexane/diethyl ether)

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).

Source