Trifluoromethanesulfonic anhydride → 5-Bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate

HRID 2207049Notes

Reaction equation

HRID 2207049 reaction equation
Br.[Br:2][C:3]1[C:12]([OH:13])=[C:11]([CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([CH3:15])=[N:8]2.[O:16](S(C(F)(F)F)(=O)=O)[S:17]([C:20]([F:23])([F:22])[F:21])(=O)=[O:18]>ClCCl.N1C=CC=CC=1>[F:21][C:20]([F:23])([F:22])[S:17]([O:13][C:12]1[C:3]([Br:2])=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:14])[N:8]=[C:7]([CH3:15])[CH:6]=[CH:5]2)(=[O:18])=[O:16]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 896765605-bromo-2,7-dimethylquinolin-6-ol-HBr

Product 1

HCID 866919775-Bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-bromo-2,7-dimethylquinolin-6-ol-HBr (1.04 g, 3.1 mmol) in dichloromethane (50 mL) and pyridine (10 mL) was added Tf2O (1.1 mL, 6.2 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours, quenched with slow addition of NaHCO3 solution at 0° C. The mixture was extracted with dichloromethane. The organic layer was washed with brine and dried with Na2SO4. Concentration gave 5-bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate as a brown solid.

Workup

  1. customquenched with slow addition of NaHCO3 solution at 0° C
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-926bc67382e94962b3aa6a1307a8259b
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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