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

HRID 1788859Notes

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>>[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

Reactant 2

HCID 24386Thionyl Chloride

HCID 44073Acifluorfen

Product 1

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

Procedure

0.3 Part of 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid and 0.83 part of thionyl chloride for 2 hours. After the reaction, the excess of thionyl chloride was removed under reduced pressure to give 0.31 part of 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride. The resulting benzoyl chloride was added dropwise to a mixture of 0.14 part of diethylaminomethyl phosphonate, 0.095 part of triethylamine and 6 parts by volume of benzene with ice cooling. After the addition, the mixture was stirred at room temperature for 4 hours, and water was added. The mixture was then extracted with benzene, and the extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 0.3 part of the desired compound (100). The IR and NMR spectral data of the compound are shown in Table 1.

Workup

customAfter the reaction
customthe excess of thionyl chloride was removed under reduced pressure

Sources & evidence

ORD record: ord-7bca2b98e81b4d6c8d6a97745045e45b
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04685952

Reaction notes

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