Reaktion #40666

ord-c8b49cfec5fa471483c52646642798ca

Reaktionsgleichung

CC1(C)CNc2ccccc21
2c
CC1(C)CNc2ccccc21
3,3-dimethylindoline
O=[N+]([O-])c1ccccc1F
1-fluoro-2-nitrobenzene
CC1(C)CN(c2ccccc2[N+](=O)[O-])c2ccccc21
2d
Ausbeute 95.0%
CC1(C)CN(c2ccccc2[N+](=O)[O-])c2ccccc21
3,3-dimethyl-1-(2-nitrophenyl)indoline
Ausbeute 95.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
175°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with 1N HCl
  2. 2
    Trocknendried over Na2SO4
  3. 3
    SonstigeThe solvent was evaporated under reduced pressure
  4. 4
    Sonstigepurified by column chromatography
  5. 5
    Sonstigeover 30 min
  6. 6
    Waschenas eluting solvent

Vorschrift

To 2c (317 mg, 2.12 mmol) was added 1-fluoro-2-nitrobenzene (200 mg, 1.42 mmol). The reaction mixture was stirred at 175° C. for 8 h. The reaction mixture was diluted with CH2Cl2 and washed with 1N HCl and dried over Na2SO4. The solvent was evaporated under reduced pressure and purified by column chromatography using 0 to 10% EtOAc in hexane over 30 min as eluting solvent to afford 2d (360 mg, 95%) as an oil. MS (ES) m/z 269 [M+H]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728008B2uspto-grants-2010_06