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Iron (33 g, 0.59 mol) was added to 2-fluoro-1-methylsulfanyl-4-nitro-benzene (18.5 g, 99 mmol) in a mixture of acetic acid (350 mL) and water (70 mL). The mixture was stirred for 2 h with periodic swirling, and then the solvents were evaporated. Ethyl acetate and aqueous sodium bicarbonate solution were added and the mixture was filtered through Celite. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate), filtered, evaporated, and purified by column chromatography, eluting with 20% ethyl acetate/hexanes to give 3-fluoro-4-methylsulfanyl-phenylamine (15.1 g, 97%).

1. customthe solvents were evaporated
2. additionEthyl acetate and aqueous sodium bicarbonate solution were added
3. filtrationthe mixture was filtered through Celite
4. extractionThe aqueous layer was extracted three times with ethyl acetate
5. washThe combined organic layers were washed with brine
6. dry with materialdried (sodium sulfate)
7. filtrationfiltered
8. customevaporated
9. custompurified by column chromatography
10. washeluting with 20% ethyl acetate/hexanes