Diethyl Ether → HCID 46224324, compound

HRID 2369445Notes

Reaction equation

HRID 2369445 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([F:4])[F:3].[F:20][C:21]([F:27])([F:26])[S:22]([OH:25])(=[O:24])=[O:23].CCOCC>C(Cl)Cl.C(#N)C>[F:20][C:21]([F:27])([F:26])[S:22]([O-:25])(=[O:24])=[O:23].[F:1][C:2]([F:4])([F:3])[S+:5]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]1=2

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 62406Trifluoromethanesulfonic acidHCID 46224400HCID 46224400, compound

Product 1

HCID 46224324HCID 46224324, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-80 °C

Procedure

A solution of (trifluoromethyl)-(2-(2-phenylethynyl)phenyl)sulfide (1.5 g, 5.4 mmol) prepared in Example 2 in 10 ml of methylene chloride was charged into a 50-ml eggplant flask equipped with a stirrer, and cooled to −80° C. Then, trifluoromethanesulfonic acid (1.62 g, 10.8 mmol) was added dropwise to the solution, and the solution was gradually heated to room temperature, and stirred overnight. After completion of the reaction, a solvent was removed, ether was added to the obtained residue to cause solidification, and the solidified product was filtered and washed with ether. The obtained crude product was dissolved in acetonitrile, and ether was added to the solution to cause crystallization to obtain target S-(trifluoromethyl)-2-phenylbenzo[b]thiophenium trifluoromethanesulfonate (1.8 g, 80%).

Workup

  1. customequipped with a stirrer
  2. temperaturethe solution was gradually heated to room temperature
  3. customAfter completion of the reaction
  4. customa solvent was removed
  5. additionether was added to the obtained residue
  6. filtrationthe solidified product was filtered
  7. washwashed with ether
  8. customThe obtained crude product
  9. customcrystallization

Sources & evidence

ORD record
ord-7f539fca86644e94a37fbf7afdd281cd
Source dataset
uspto-grants-2014_04
Patent number
US08703969B2

Reaction notes

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