2-Chloro-1-(methylsulfanyl)-4-nitrobenzene → 3-Chloro-4-(methylthio)aniline

To a mixture of the compound from stage (i) (14.08 g, 69 mmol) in acetic acid (300 mL) and water (60 mL) was added Fe powder (23 g, 412 mmol) and the reaction mixture was swirled until all the starting material had dissolved. The mixture was left to stand for 1.5 h and the acetic acid was then removed under reduced pressure. The residue was taken up in sat NaHCO3 (aq) (500 mL) and EtOAc (500 mL) and filtered through Arbacel®. The layers were separated, the aqueous phase was extracted with EtOAc (300 mL) and the combined organics were washed with brine, dried (MgSO4) and the solvent was removed in vacuo to give the title compound (11.52 g, 96%) as a beige solid; δH (400 MHz, CDCl3) 2.38 (3H, s), 3.66 (2H, br), 6.53 (1H, dd), 6.70 (1H, d), 7.12 (1H, d); MS m/z (ES+) 174 (MH+).

1. dissolutionhad dissolved
2. waitThe mixture was left
3. customthe acetic acid was then removed under reduced pressure
4. filtrationEtOAc (500 mL) and filtered through Arbacel®
5. customThe layers were separated
6. extractionthe aqueous phase was extracted with EtOAc (300 mL)
7. washthe combined organics were washed with brine
8. dry with materialdried (MgSO4)
9. customthe solvent was removed in vacuo

ORD record

ord-d671c11fa996498a8d3a3753837a64b9

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129234B2