Toluene → HCID 13090781, compound

HRID 1252651Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)[CH2:8]O.C1(C)C=CC=CC=1.S(Cl)([Cl:33])=O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)[CH2:8][Cl:33]

Participants

Conditions

Temperature: 110 °C

Procedure

34.8 parts by weight of 3-(2'-chloro-4'-trifluoromethylphenoxy)-6-nitrobenzyl alcohol were suspended in 200 parts by volume of absolute toluene, 8 parts by weight of pyridine were added, and 13.1 parts by weight of thionyl chloride were added dropwise at 0° C. Thereafter the reaction mixture was stirred for a further 2 hours at 110° C., was cooled, and was extracted with 75 parts by volume of 3N hydrochloric acid and with five times 250 parts by volume of water. The organic phase was separated off, dried with magnesium sulfate and concentrated under reduced pressure. 32 parts by weight (88% of theory) of 3-(2'-chloro-4'-trifluoromethylphenoxy)-6-nitrobenzyl chloride were obtained in the form of an initially oily residue which crystallized when triturated with pentane, to give crystals of melting point 55°-60° C.

Workup

additionwere added
temperaturewas cooled
extractionwas extracted with 75 parts by volume of 3N hydrochloric acid and with five times 250 parts by volume of water
customThe organic phase was separated off
dry with materialdried with magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2a5f19be34174316b62d2718c98881f3
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04744812

Reaction notes

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