Hydrochloric Acid → 1-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one

HRID 645298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645298
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][C:10]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)(O)[C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[CH3:25].S(Cl)(Cl)=O.N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH:9]=[C:10]([C:16]2[CH:17]=[C:18]([Cl:23])[CH:19]=[C:20]([Cl:22])[CH:21]=2)[C:11]([F:13])([F:14])[F:12])=[CH:4][C:3]=1[CH3:25]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 866264261-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one

Produkt 1

HCID 765635821-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-oneAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 0.3 g of 1-(4-bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-3-hydroxy-4,4,4-trifluorobutane-1-one synthesized under Synthetic Example 1 in 3 g toluene, 0.391 g of thionyl chloride and 0.104 g of pyridine were added at room temperature and the mixture was stirred for 1 hour at 80° C. After the end of reaction, the reaction solution was cooled to room temperature, added with toluene and 2N hydrochloric acid and separated, and then an organic layer was washed with water and dried with anhydrous magnesium sulfate to distill off the solvent under reduced pressure. The resulting residue, which although contains mixed geometrical isomers, was purified using silica gel column chromatography that was eluted with ethyl acetate-hexane (1:10), and 0.244 g of aimed product was obtained as yellow solid.

Aufarbeitung

  1. customAfter the end of reaction
  2. temperaturethe reaction solution was cooled to room temperature
  3. customseparated
  4. washan organic layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationto distill off the solvent under reduced pressure
  7. additionThe resulting residue, which although contains mixed geometrical isomers
  8. customwas purified
  9. washwas eluted with ethyl acetate-hexane (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-e22aed4b04c84b249e30a302909ddcc8
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700808B2

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