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

HRID 1903346Notes

Reaction equation

HRID 1903346 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](O)=[O:11].S(Cl)([Cl:27])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([Cl:27])=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 44073Acifluorfen

Product 1

HCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chlorideYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid (448.1 g, 1.24 mole), thionyl chloride (458 g) and toluene (250 ml) was held at reflux for 8 hrs. The excess thionyl chloride and the solvent were stripped off under reduced pressure to give a reddish solid, which upon recrystallization from hexane-toluene afforded 282.9 g of the desired benzoyl chloride as a light yellow crystalline solid; mp 63°-69° C.

Workup

  1. temperatureat reflux for 8 hrs
  2. customto give a reddish solid, which
  3. customupon recrystallization from hexane-toluene

Sources & evidence

ORD record
ord-84b98349d6a8427b890031cada543656
Source dataset
uspto-grants-1984_03
Patent number
US04435588

Reaction notes

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