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Methane → 5-[2,6-Dichloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride

HRID 1719655
Notes
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Reaction equation

HRID 1719655 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([Cl:25])[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]([OH:12])=O.CN(C)C=O.S(Cl)([Cl:33])=O.C>ClCCCl>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:18]=[C:17]([Cl:25])[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:33])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 297MethaneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 13013695HCID 13013695, compound

Product 1

HCID 129267235-[2,6-Dichloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chlorideYield 79%

Reagents, catalysts & solvents 1

HCID 11
1,2-Dichloroethane
Solvent

Procedure

79.2 g of 5-(2,6-dichloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid and 0.5 ml of dimethylformamide were introduced into 150 ml of 1,2-dichloro-ethane. 28.6 g of thionyl chloride were added dropwise at 60° to 65° C. and the mixture was heated under reflux for 1 hour. The solution was clarified with active charcoal and filtered through kieselguhr. The mother liquor was concentrated and the residue was recrystallized from cyclohexane. 65.1 g (79% of theory) of 5-(2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-benzoic acid chloride, of melting point 95° C., were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. filtrationfiltered through kieselguhr
  4. concentrationThe mother liquor was concentrated
  5. customthe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-bdadccf9abef4974bb34961af050a019
Source dataset
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04540827

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes