Diphosgene → 1-Bromo-4-isocyanato-2-(trifluoromethyl)benzene

HRID 78325

Reaktionsgleichung

Reaktionsgleichung von HRID 78325
Cl.[Br:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[C:10]([F:13])([F:12])[F:11].Cl[C:15](OC(Cl)(Cl)Cl)=[O:16]>C1(C)C=CC=CC=1>[Br:2][C:3]1[CH:9]=[CH:8][C:6]([N:7]=[C:15]=[O:16])=[CH:5][C:4]=1[C:10]([F:11])([F:12])[F:13]

Komponenten

4

Edukt 2

HCID 10426DiphosgeneHCID 667457074-bromo-3-(trifluoromethyl)aniline HCl salt

Produkt 1

HCID 231372171-Bromo-4-isocyanato-2-(trifluoromethyl)benzeneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 4-bromo-3-(trifluoromethyl)aniline HCl salt (36.8 g, 133 mmol) in toluene (278 mL) was treated with trichloromethyl chloroformate dropwise and the resulting mixture was heated at the reflux temp. for 18 h. The resulting mixture was concentrated under reduced pressure. The residue was treated with toluene (500 mL), then concentrated under reduced pressure. The residue was treated with CH2Cl2 (500 mL), then concentrated under reduced pressure. The CH2Cl2 treatment/concentration protocol was repeated and resulting amber oil was stored at −20° C. for 16 h, to afford 4-bromo-3-(trifluoromethyl)phenyl isocyanate as a tan solid (35.1 g, 86%): GC-MS m/z 265 (M+).

Aufarbeitung

  1. temperaturethe resulting mixture was heated at the reflux temp
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additionThe residue was treated with toluene (500 mL)
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was treated with CH2Cl2 (500 mL)
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe CH2Cl2 treatment/concentration protocol
  8. customresulting amber oil
  9. waitwas stored at −20° C. for 16 h

Quellen und Nachweise

ORD-Eintrag
ord-2f5394f539234064b469c6fd13c69670
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841330B2

Verknüpfte Notizen

Wird geladen…