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

HRID 2295953Notes

Reaction equation

HRID 2295953 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. Aftr this time the reaction mixture was stripped of toluene to yield the desired product 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride.

Workup

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

Sources & evidence

ORD record
ord-0c7550646ad841298e0a2f340e6b5ec4
Source dataset
uspto-grants-1984_01
Patent number
US04427441

Reaction notes

Loading…