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Trifluoroacetic anhydride → 5-Bromo-2-chloro-1-oxo-1lambda~5~-pyridine

HRID 1693085
Notes
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Reaction equation

HRID 1693085 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[N:19][CH:20]=1.C(N)(N)=O.OO.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[N+:19]([O-:4])[CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 108762Thiosulfuric acid, disodium salt, monohydrateHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 162183245-Bromo-2-chloro-1-oxo-1lambda~5~-pyridineYield 78.1%

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Procedure

With cooling with ice, trifluoroacetic anhydride (11.9 mL, 84.2 mmol) was added to a chloroform (50 mL) solution of 5-bromo-2-chloropyridine (8.1 g, 42.1 mmol) and percarbamide (8.3 g, 88.4 mmol), and stirred at room temperature for 1 hour. Sodium thiosulfate water was added to the reaction mixture, then stirred at room temperature for 40 minutes, and extracted twice with chloroform. The organic layer was washed with saturated sodium bicarbonate water and saturated brine, dried with anhydrous sodium sulfate and concentrated under reduced pressure. Ethyl acetate was added to the residue, and the resulting solid was taken out through filtration, washed with diethyl ether and dried to obtain the entitled compound (6.85 g, 78%) as a yellow solid.

Workup

  1. stirringstirred at room temperature for 40 minutes
  2. extractionextracted twice with chloroform
  3. washThe organic layer was washed with saturated sodium bicarbonate water and saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionEthyl acetate was added to the residue
  7. filtrationthe resulting solid was taken out through filtration
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-71a6dac0bf9d4ae2bb8022b490f1168c
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158652B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes