2-Nitropropane → HCID 12696803, compound

Temperature

0 °C

2-Nitropropane (3.19 mL, 35.5 mmol) was added to a mixture of sodium hydride (0.85 g, 35 mmol) in methanol (15 mL) cooled to 0° C. The reaction mixture was then stirred and allowed to warm to 25° C. for 10 min. The solvent was rotary evaporated to provide a white solid. A mixture of this solid and N-(2-chlorobenzyl)-2,4,6-triphenylpyridinium tetrafluoroborate (6.14 g, 11.8 mmol) in dimethyl sulfoxide (45 mL) was stirred under nitrogen gas for 16 h. Water was then added to quench the reaction. This mixture was then extracted with diethyl ether (3×100 mL). The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), and filtered. The filtrate was stirred in strongly acidic Amberlyst 15 ion-exchange resin (1 g/mmol) for 4 h. The reaction mixture was filtered and rotary evaporated. This provided 2.35 g (93%) of 1-(2-chlorophenyl)-2-methyl-2-nitropropane.

1. temperatureto warm to 25° C. for 10 min
2. customThe solvent was rotary evaporated
3. customto provide a white solid
4. stirringwas stirred under nitrogen gas for 16 h
5. customto quench
6. customthe reaction
7. extractionThis mixture was then extracted with diethyl ether (3×100 mL)
8. washThe organic layer was washed with saturated aqueous sodium chloride
9. dry with materialdried (anhydrous sodium sulfate)
10. filtrationfiltered
11. stirringThe filtrate was stirred in strongly acidic Amberlyst 15 ion-exchange resin (1 g/mmol) for 4 h
12. filtrationThe reaction mixture was filtered

ORD record

ord-9efdf4f9ce7849c2b3759fdf5b2bf4be

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07053104B2