Water → 2-(4-Nitrophenyl)propanenitrile

Temperature

-15 °C

A −15° C. solution of 4-nitroacetophenone (16.5 g, 100 mmol) and tosylmethyl isocyanide (2.9.3 g, 150 mmol) in methoxyethyl ether (400 mL) was slowly treated with a room temperature solution of the potassium t-butbxide. (28 g, 250 mmol) in t-butanol (200 mL). The reaction mixture was stirred at −15° C. for 1 h and then allowed to warm to room temperature over night. Water (100 mL) was added to the mixture and the organic layer was extracted with ether (3×200 mL). The combined organic fraction was washed with water (3×200 mL), brine (100 mL), dried over sodium sulfate, and concentrated in vacuo to give the crude material which was further purified by flash chromatography (SiO2, 30% EtOAc: Hexane) to give 13.6 g (77%) of the title compound. The NMR spectrum was consistent with the proposed title structure. Field Desorption Mass Spectrum: M+=176.

1. temperatureto warm to room temperature over night
2. extractionthe organic layer was extracted with ether (3×200 mL)
3. washThe combined organic fraction was washed with water (3×200 mL), brine (100 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customto give the crude material which
7. customwas further purified by flash chromatography (SiO2, 30% EtOAc: Hexane)

ORD record

ord-632640bc25734e008ee0ec1c189eac94

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06693137B1