Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-(5-bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

HRID 545090Notes

Reaction equation

HRID 545090 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[Br-:15].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1>[Br:15][CH2:9][C:8]([C:5]1[C:4]([C:11]([F:14])([F:12])[F:13])=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:10]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 586455621-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

Product 1

HCID 866051072-Bromo-1-(5-bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1-(5-bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone (0.7 g, 0.0026 mol) in anhydrous THF at room temperature under N2 atmosphere. Add phenyltrimethyl-ammonium tribromide (1.47 g, 0.0039 moles, 1.5 eq.) to the reaction mixture and reflux overnight. Cool the reaction mixture to room temperature, filter the insoluble solid and concentrate the filtrate under vacuum. Purify by column chromatography to afford the title compound as a yellow oil.

Workup

  1. filtrationfilter the insoluble solid
  2. concentrationconcentrate the filtrate under vacuum
  3. customPurify by column chromatography

Sources & evidence

ORD record
ord-663cd03b059e4557847927ba69c5b95b
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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