Iodoethane → HCID 55220820, compound

Temperature

80 °C

To thick-walled reaction pressure tube was added 3,4-difluorobenzenethiol (1500 mg, 10.26 mmol), iodoethane (1.095 mL, 13.34 mmol), acetonitrile (20 mL), and triethylamine (1.860 mL, 13.34 mmol). The vessel was capped and heated at 80° C. for 2 hours. After cooling to room temperature, the reaction mixture was concentrated. Methylene chloride was added and the mixture was washed with water three times. The organic layer was concentrated to provide crude 4-(ethylthio)-1,2-difluorobenzene which was used without further purification. This material was combined with 2-propanol (20 mL) and water (10 mL). To the mixture was added OXONE® (8388 mg, 13.7 mmol). After stirring at room temperature overnight, the reaction mixture was evaporated in vacuo and the residue was extracted with ethyl acetate. The ethyl acetate was washed with water three times followed by saturated aqueous sodium bicarbonate and then brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The resulting residue was purified by flash chromatography (silica gel, 0-100% ethyl acetate/hexane) to give Intermediate 8 (2 g, 99% yield) as white solid. 1H NMR (CDCl3, 500 MHz) δ 7.67-7.82 (m, 2H), 7.38 (dd, J=16.22, 9.07 Hz, 1H), 3.13 (q, J=7.70 Hz, 2H), 1.25-1.32 (m, 3H); MS (ESI) 207.1 (M+H).

1. customTo thick-walled reaction pressure tube
2. customThe vessel was capped
3. temperatureAfter cooling to room temperature
4. concentrationthe reaction mixture was concentrated
5. additionMethylene chloride was added
6. washthe mixture was washed with water three times
7. concentrationThe organic layer was concentrated

ORD record

ord-87ac6f6e91e64693aaa6f644cce664db

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415367B2