Diethyl Ether → HCID 46183783, compound

HRID 2369442Notes

Reaction equation

HRID 2369442 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:12][C:13]([F:16])([F:15])[F:14])[CH2:3][CH2:2]1.C(Cl)Cl.[F:20][C:21]([F:27])([F:26])[S:22]([OH:25])(=[O:24])=[O:23].CCOCC>C(#N)C>[O-:25][S:22]([C:21]([F:27])([F:26])[F:20])(=[O:24])=[O:23].[CH:1]1([C:4]2[S+:12]([C:13]([F:16])([F:14])[F:15])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 62406Trifluoromethanesulfonic acidHCID 69670549HCID 69670549, compound

Product 1

HCID 46183783HCID 46183783, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-50 °C

Procedure

1-cyclopropylethynyl-2-trifluoromethylsulfanylbenzene (0.67 g, 2.77 mmol) prepared in Example 1 and anhydrous methylene chloride (5 ml) were charged into a 25-ml round-bottomed flask equipped with a stirrer, and cooled to −50° C. with stirring. To this mixture, trifluoromethanesulfonic acid (0.5 ml, 5.54 mmol) was added dropwise, and the solution was heated, and stirred at room temperature overnight. After completion of the reaction, a solvent was removed, ether (10 ml) was added to form a deposit, and the deposit was collected by filtration. The obtained crude product was dissolved in acetonitrile. After then, ether was added to form a precipitation, which was collected by filtration. This operation was repeated three times to purify the product. After the purification, target 2-cyclopropyl-1-trifluoromethylbenzo[b]thiophenyl triflate was obtained as a white solid (0.87 g, yield: 80%).

Workup

  1. customequipped with a stirrer
  2. temperaturethe solution was heated
  3. stirringstirred at room temperature overnight
  4. customAfter completion of the reaction
  5. customa solvent was removed
  6. additionether (10 ml) was added
  7. customto form a deposit
  8. filtrationthe deposit was collected by filtration
  9. customThe obtained crude product
  10. customto form
  11. customa precipitation, which
  12. filtrationwas collected by filtration
  13. customto purify the product
  14. customAfter the purification

Sources & evidence

ORD record
ord-710358278c9542189755cf16997cab32
Source dataset
uspto-grants-2014_04
Patent number
US08703969B2

Reaction notes

Loading…