Propyl mercaptan → Nitrobenzene

Temperature

50 °C

Into a pressure bottle was placed 2-chloro-4-nitrophenol (15.0 g, 0.086 mole), potassium carbonate (11.9 g, 0.86 mole), propanethiol (1.5 g, 0.02 mole), 1,2-dibromotetrafluoroethane (33.7 g, 0.13 mole), and N,N-dimethylformamide (115 ml). The pressure bottle was sealed, and the mixture was stirred at 50° C. for 48 hours. The pressure bottle was cooled to room temperature, opened, and the contents poured into a separatory funnel. Approximately 200 ml of a 2N aqueous sodium hydroxide solution was added to the separatory funnel. The resultant mixture was extracted with four 300 ml portions of diethyl ether. The extracts were combined and washed with two 100 ml portions of a 2N aqueous sodium hydroxide solution. The washed extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, leaving an oil. The reaction described above was repeated three additional times. The residual oils from the four experiments were combined and purified by column chromatography on silica gel, eluting with n-heptane:toluene (95:5), yielding 57.6 g of 3-chloro-4-bromo-1,1,2,2-tetrafluoroethoxy)nitrobenzene as an oil.

1. customThe pressure bottle was sealed
2. temperatureThe pressure bottle was cooled to room temperature
3. additionthe contents poured into a separatory funnel
4. extractionThe resultant mixture was extracted with four 300 ml portions of diethyl ether
5. washwashed with two 100 ml portions of a 2N aqueous sodium hydroxide solution
6. extractionThe washed extract
7. dry with materialwas dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customThe filtrate was evaporated under reduced pressure
10. customleaving an oil
11. custompurified by column chromatography on silica gel
12. washeluting with n-heptane:toluene (95:5)

ORD record

ord-1bfa0952a03c4acc99b001e78a6536d0

Source dataset

uspto-grants-1989_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04870089