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Toluene → HCID 13090781, compound

HRID 1252651
Notes
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Reaction equation

HRID 1252651 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 13050461HCID 13050461, compound

Product 1

HCID 13090781HCID 13090781, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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

  1. additionwere added
  2. temperaturewas cooled
  3. extractionwas extracted with 75 parts by volume of 3N hydrochloric acid and with five times 250 parts by volume of water
  4. customThe organic phase was separated off
  5. dry with materialdried with magnesium sulfate
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes