Thionyl Chloride → 5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

HRID 2290683Notes

Reaction equation

HRID 2290683 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[Cl:24])=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].S(Cl)([Cl:27])=O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[Cl:24])=[CH:9][C:5]=1[C:6]([Cl:27])=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 44073Acifluorfen

Product 1

HCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid (80 grams) and toluene (80 ml) were charged into a reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. Thionyl chloride (80 ml) was slowly added at room temperature with stirring. After the addition was completed, the mixture was heated at reflux with continued stirring for a period of one hour. Stirring was thereafter continued at room temperature overnight. After this time the reaction mixture was stripped of toluene to yield the desired product as an oil.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionAfter the addition
  4. temperaturethe mixture was heated
  5. temperatureat reflux
  6. stirringwith continued stirring for a period of one hour
  7. stirringStirring

Sources & evidence

ORD record
ord-a4c4c3342db04ceb84c38365d763ccc8
Source dataset
uspto-grants-1986_10
Patent number
US04618359

Reaction notes

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