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

HRID 2207018
Notes
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Reaction equation

HRID 2207018 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-cb286cb5921547198c42f5c01b3f6e90
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376392B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes