Benzyl chloroformate → HCID 10495292, compound

Temperature

0 °C

A solution of 6.0 g(28.82 mmol) of 3-fluoro-1-nitro-4-(2H-1,2,3-triazol-2-yl)benzene in 150 mL ethyl acetate and 25 mL methanol was treated with 750 mg of W-2 Raney Nickel. The mixture was hydrogenated on a Paar shaker under 45psi hydrogen pressure for 24 h. The mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was dissolved in 150 mL acetone, treated with 72 mL saturated sodium bicarbonate solution, followed by cooling to 0 ° C. The mixture was treated with 6.15 g(5.14 mL, 36.08 mmol) of benzyl chloroformate, followed by stirring at 0° C. for 1 h, and then warming to ambient temperature for 3 h. The mixture was diluted with 500 mL water and 400 mL ethyl acetate. The aqueous phase was washed with 250 mL ethyl acetate and the combined organic layers were extracted with 300 mL saturated NaCl solution. Drying (Na2SO4) and concentration in vacuo afforded an amber oil which was recrystallized from hot chlorform-hexane to afford 7.52 g(84%) of the title compound as a white solid, mp 99.5-101° C.

1. filtrationThe mixture was filtered through celite
2. concentrationthe filtrate was concentrated in vacuo
3. dissolutionThe residue was dissolved in 150 mL acetone
4. additiontreated with 72 mL saturated sodium bicarbonate solution
5. temperaturewarming to ambient temperature for 3 h
6. washThe aqueous phase was washed with 250 mL ethyl acetate
7. extractionthe combined organic layers were extracted with 300 mL saturated NaCl solution
8. customDrying
9. concentration(Na2SO4) and concentration in vacuo
10. customafforded an amber oil which
11. customwas recrystallized from hot chlorform-hexane

ORD record

ord-fdd4ba0ddeb84cadbc15cd49e24bf036

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06124334