Thionyl Chloride → 2,4-Dichloro-3-cyano-5-fluorobenzoyl chloride

HRID 916275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916275
S(Cl)(Cl)=O.[C:5]([C:7]1[C:8]([Cl:18])=[C:9]([CH:13]=[C:14]([F:17])[C:15]=1[Cl:16])[C:10](O)=[O:11])#[N:6].[ClH:19].S(=O)=O>N1C=CC=CC=1>[C:5]([C:7]1[C:8]([Cl:18])=[C:9]([CH:13]=[C:14]([F:17])[C:15]=1[Cl:16])[C:10]([Cl:19])=[O:11])#[N:6]

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 109005412,4-Dichloro-3-cyano-5-fluorobenzoic acidHCID 22338718Hydrogen chloride sulphur dioxide

Produkt 1

HCID 143001312,4-Dichloro-3-cyano-5-fluorobenzoyl chlorideAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

4100 ml of thionyl chloride and 41 ml of pyridine were introduced into a stirred apparatus fitted with metering device and gas outlet leading to a scrubber via a reflux condenser, and, at 20° C., 2050 g of 3-cyano-2,4-dichloro-5-fluorobenzoic acid (99.5% strength) were introduced at the rate of hydrogen chloride/sulphur dioxide evolution. At the end of the addition, the mixture was heated to reflux until the evolution of gas ceased. The mixture was then distilled. In the boiling range from 142 to 145° C./10 mbar, 2150 g (95.7% of theory) of 3-cyano-2,4-dichloro-5-fluorobenzoyl chloride were obtained (content according to GC: 98.0%).

Aufarbeitung

  1. customfitted with metering device and gas outlet
  2. customleading to a scrubber via a reflux condenser
  3. additionAt the end of the addition
  4. temperaturethe mixture was heated
  5. temperatureto reflux until the evolution of gas
  6. distillationThe mixture was then distilled

Quellen und Nachweise

ORD-Eintrag
ord-07df0b35ca9d4ff28a680b8dbe2ee40d
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268248B2

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