Dimethyl Sulfoxide → 2-Chloro-6-nitro-benzenethiol

To a solution of 2,3-dichloronitrobenzene (Aldrich, 19.2 g, 100 mmol) in 300 mL of DMSO was added powdered Na2S.9H2O (Aldrich, 24.0 g, 100 mmol). The mixture was stirred at ambient temperature for 24 h, then was diluted with 2 L of water. The mixture was clarified by filtration and the filtrate was acidified to pH 4 with con. HCl. The mixture was extracted 3× with Et2O (400 mL). The organic layers were combined and washed twice with a brine solution (400 mL), dried over Na2SO4. Removal of the solvent under reduced pressure gave 18.4 g product. 1H NMR (400 MHz, DMSO) δ 8.11 (dd, J=8.3, 1.3 Hz, 1H), 7.93 (dd, J=8.0, 1.3 Hz, 1H), 7.40 (td, J=8.2, 1.3 Hz, 1H) 5.06 (s, 1H). MS (EI): m/z 188 (M−H).

1. filtrationThe mixture was clarified by filtration
2. extractionThe mixture was extracted 3× with Et2O (400 mL)
3. washwashed twice with a brine solution (400 mL)
4. dry with materialdried over Na2SO4
5. customRemoval of the solvent under reduced pressure

ORD record

ord-76a6e7c2031b41669e1ada70de5d905b

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601841B2