Water → HCID 68993601, compound

To a solution of 4-chloro-3-nitrothiophenol (0.4 g) and benzyl bromide (0.3 mL) in N,N-dimethylformamide (6 mL) was added potassium carbonate (0.44 g), and the mixture was stirred at room temperature for 15 minutes. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane −n-hexane/ethyl acetate=9/1) to give 1-benzylthio-4-chloro -3-nitrobenzene (0.54 g). This material was dissolved in methanol (5 mL)-tetrahydrofuran (5 mL). To the solution were added nickel (II) bromide (21 mg) and sodium borohydride (0.22 g) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. The mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate.

1. extractionthe resulting mixture was extracted with ethyl acetate
2. washThe extract was washed with water and brine successively
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was removed under reduced pressure
5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane −n-hexane/ethyl acetate=9/1)

ORD record

ord-9c64acdc0a494450b32fa21326d9eec0

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040693B2