1-Chloro-3-(2-nitroethenyl)benzene → 1-Chloro-3-(2-nitroethyl)benzene

A solution of 13.5 g (72 mmol) of 2-(3-Chlorophenyl)-1-nitroethene, from Step 2, in 200 mL of dioxane was added dropwise to a stirred suspension of 6 g (157 mmol) of sodium borohydride in a mixture of 140 mL of dioxane and 60 mL of ethanol. The reaction mixture was stirred at ambient temperature for 2 h and then the excess borohydride was quenched with acid. The reaction mixture was concentrated in vacuo and the residue was partitioned between methylene chloride and water (4:1). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silica gel eluted with 20% methylene chloride in hexane to afford 6.3 g (48% yield) of the title compound; MS DCl--NH3M/Z: 203 (M+NH4)+ ; 1H NMR (CDCl3) δ3.3 (2H, t, J=7.5 Hz), 4.6 (2H, t, J= 7.5 Hz), 7.05-7.3 (4H, m).

1. customthe excess borohydride was quenched with acid
2. concentrationThe reaction mixture was concentrated in vacuo
3. customthe residue was partitioned between methylene chloride and water (4:1)
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified on silica gel
8. washeluted with 20% methylene chloride in hexane

ORD-Eintrag

ord-8ba885339f8d41249dc7afe4b839d218

Quelldatensatz

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05248677