Trifluoromethanesulfonic anhydride → HCID 59611359, compound

HRID 72056Notes

Reaction equation

HRID 72056 reaction equation
[O:1]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])S(C(F)(F)F)(=O)=O.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:27][C:26]3[CH:28]=[C:29](O)[CH:30]=[CH:31][C:25]=3[CH:24]=2)=[CH:19][CH:18]=1>N1C=CC=CC=1>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:27][C:26]3[CH:28]=[C:29]([O:1][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])[CH:30]=[CH:31][C:25]=3[CH:24]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 59611582HCID 59611582, compound

Product 1

HCID 59611359HCID 59611359, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Tf2O was added slowly to a mixture of 2-(4-bromo-phenyl)-benzo[b]thiophen-6-ol (200 mg, 0.66 mol) in pyridine (3 mL) at 0° C. with stirring. The mixture was stirred at ambient temperature for 16 hours before quenched with NaHCO3 solution. The mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was used for next step reaction without further purification.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 16 hours
  2. custombefore quenched with NaHCO3 solution
  3. extractionThe mixture was extracted with ethyl acetate (50 mL)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe obtained residue was used for next step reaction without further purification

Sources & evidence

ORD record
ord-02e269ceba3b404a9c16a0fe1a3c3f74
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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