Hydrochloric Acid → TRANS-BETA-NITRO-2-(TRIFLUOROMETHYL)-

Temperature

-10 °C

2-(Trifluoromethyl)benzaldehyde (0.758 mL, 5.74 mmol) was dissolved in MeOH (5 mL) and nitromethane (0.370 mL, 6.89 mmol) was added. The mixture was cooled to −10° C. and a solution of NaOH (0.241 g, 6.03 mmol) in Water (2 mL) was added slowly keeping the temperature below −5° C. The mixture stirred at −5° C. for 15 minutes then warmed to 0° C. and stirred for two hours. Ice water (6 mL) was added followed by HCl (6 N, 3 mL). The mixture was extracted with DCM (×2) and washed with brine. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give (E)-1-(2-nitrovinyl)-2-(trifluoromethyl)benzene (1.12 g, 2.373 mmol, 41%).

1. customthe temperature below −5° C
2. temperaturethen warmed to 0° C.
3. stirringstirred for two hours
4. extractionThe mixture was extracted with DCM (×2)
5. washwashed with brine
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-cc16e2b4e7e640099711b62dc0660277

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09023865B2