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

HRID 917366

Reaction equation

HRID 917366 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 86760554O-(6,6-difluoro-5-methyl-5-hexenyl) benzo[b]thiophene-2-thiocarboxylateYield 81.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-54f3d4c86d6c4f1483707799d247ea36
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Linked notes

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