Reaktion #438744

Reaktionsgleichung

HCl

Sodium hydride

(3,4-dichlorophenyl)acetonitrile

2-methoxy-1,3-dimethyl-5-nitrobenzene

→

(±)-α-(3,4-dichlorophenyl)-2,6-dimethyl-4-nitrobenzeneacetonitrile

Ausbeute 87.0%

Lösungsmittel

H2O

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at 0° C. under N2 flow for 1 hour
2. 2
   workup.ADDITIONwas added dropwise at 0° C. under N2 flow
3. 3
   workup.STIRRINGThe mixture was stirred at RT for 6 hours
4. 4
   Extraktionextracted with EtOAc
5. 5
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed several times with H2O
7. 7
   Sonstigedried
8. 8
   Filtrationfiltered
9. 9
   Sonstigethe solvent was evaporated
10. 10
    SonstigeThe residue was crystallized from DIPE
11. 11
    FiltrationThe precipitate was filtered off
12. 12
    Sonstigedried

Vorschrift

A mixture of (3,4-dichlorophenyl)acetonitrile (0.149 mol) in DMF (100 ml) was stirred at 0° C. under N2 flow. Sodium hydride (0.223 mol) was added portionwise. The mixture was stirred at 0° C. under N2 flow for 1 hour. A mixture of, 2-methoxy-1,3-dimethyl-5-nitrobenzene (0.149 mol) in DMF (100 ml) was added dropwise at 0° C. under N2 flow. The mixture was stirred at RT for 6 hours, then cooled, hydrolized with H2O and with HCl 3N and extracted with EtOAc. The organic layer was separated, washed several times with H2O, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 43.4 g (87%) of (±)-α-(3,4-dichlorophenyl)-2,6-dimethyl-4-nitrobenzeneacetonitrile (interm. 48).

Quelle