Azobisisobutyronitrile → 4-Fluorobenzoyl chloride

HRID 635545Notes

Reaction equation

HRID 635545 reaction equation
N(C(C)(C)C#N)=NC(C)(C)C#N.[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.[Cl:22]Cl>>[F:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]([Cl:22])=[O:19])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 24526Chlorine3×HCID 680234-Fluorobenzaldehyde

Product 1

HCID 678794-Fluorobenzoyl chloride

Conditions

Temperature
60 °C

Procedure

10 g of azobis(isobutyronitrile) are added, with stirring, to 620 g of 4-fluorobenzaldehyde (5 mol tel quel, purity >99 GC[a/a]) under protective gas in a 1 l four-necked flask. The mixture is then heated to an internal temperature of 60° C. and, over the course of 7.5 hours, a total of 354 g of chlorine are introduced. The chlorine is added in an amount of 15 liters per hour. Unreacted chlorine is then blown out with nitrogen, and the reaction mixture is cooled to room temperature. The progress of the reaction is monitored using gas-chromatographic analysis (GC).

Workup

  1. temperaturethe reaction mixture is cooled to room temperature

Sources & evidence

ORD record
ord-f7ae0a4f0e374b588f097d65fb39c8c0
Source dataset
uspto-grants-2001_02
Patent number
US06187952B1

Reaction notes

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