Trifluoromethanesulfonic anhydride → 5-Bromo-7-methylquinolin-6-yl trifluoromethanesulfonate

HRID 931745Notes

Reaction equation

HRID 931745 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[C:10]([CH3:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[O:14](S(C(F)(F)F)(=O)=O)[S:15]([C:18]([F:21])([F:20])[F:19])(=O)=[O:16]>ClCCl.N1C=CC=CC=1>[F:19][C:18]([F:21])([F:20])[S:15]([O:12][C:11]1[C:2]([Br:1])=[C:3]2[C:8](=[CH:9][C:10]=1[CH3:13])[N:7]=[CH:6][CH:5]=[CH:4]2)(=[O:16])=[O:14]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 230783095-Bromo-6-hydroxy-7-methyl-quinoline

Product 1

HCID 866919795-Bromo-7-methylquinolin-6-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 5-bromo-7-methylquinolin-6-ol (238 mg, 1.0 mmol) in dichloromethane (10 mL) and pyridine (2 mL) was added Tf2O (0.34 mL, 2.0 mmol) at −30° C. The mixture was stirred and warmed to 0° C. over a period of 2 hours. The reaction was quenched with slow addition of NaHCO3 solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give 5-bromo-7-methylquinolin-6-yl trifluoromethanesulfonate. LCMS-ESI+ (m/z): 369.9, 371.9 (M+H)+.

Workup

  1. customThe reaction was quenched with slow addition of NaHCO3 solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f4effb2ded47473bac12b94d9289bb29
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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