2-Chlorotoluene → O-(6,6-difluoro-5-methyl-5-hexenyl) benzo[b]thiophene-2-thiocarboxylate

HRID 917366

Reaktionsgleichung

Reaktionsgleichung von HRID 917366
ClC1C=CC=CC=1C.[S:9]1[C:13]([C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:25])=[C:22]([F:24])[F:23])=O)=[CH:12][C:11]2[CH:26]=[CH:27][CH:28]=[CH:29][C:10]1=2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1.C(OC(C)C)(C)C>CCCCCC>[S:9]1[C:13]([C:14](=[S:39])[O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:25])=[C:22]([F:24])[F:23])=[CH:12][C:11]2[CH:26]=[CH:27][CH:28]=[CH:29][C:10]1=2

Komponenten

6

Edukt 4

HCID 72382-ChlorotolueneHCID 7914Diisopropyl EtherHCID 87949Lawesson's reagentHCID 691816906,6-Difluoro-5-methyl-5-hexenyl benzo[b]thiophene-2-carboxylate

Produkt 1

HCID 86760554O-(6,6-difluoro-5-methyl-5-hexenyl) benzo[b]thiophene-2-thiocarboxylateAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To 5 ml of 2-chlorotoluene was dissolved 0.20 g (0.64 mmol) of 6,6-difluoro-5-methyl-5-hexenyl benzo[b]thiophene-2-carboxylate, followed by the addition of 0.26 g (0.64 mmol) of Lawesson's reagent and stirring by heating under refluxing for 4 hours. To the reaction liquid were added 2 ml of isopropyl ether and 10 ml of hexane and precipitated solid was filtered off. The filtrate was concentrated under reduced pressure and the residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:30) to obtain 0.17 g (yield: 81%) of O-(6,6-difluoro-5-methyl-5-hexenyl) benzo[b]thiophene-2-thiocarboxylate.

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder refluxing for 4 hours
  3. customTo the reaction liquid
  4. customprecipitated solid
  5. filtrationwas filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:30)

Quellen und Nachweise

ORD-Eintrag
ord-54f3d4c86d6c4f1483707799d247ea36
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273878B2

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