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

HRID 55990Notes

Reaction equation

HRID 55990 reaction equation
[Cl:1][C:2]1[C:3]([C:12](=[O:14])[CH3:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Br-:15].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C>O1CCCC1>[Br:15][CH2:13][C:12]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:5][N:4]=1)=[O:14]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 217121361-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-ethanone

Product 1

HCID 860575962-Bromo-1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethanoneYield 222.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.82 g of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone in 10 ml of tetrahydrofuran, 1.38 g of trimethylphenylammonium tribromide was added, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the precipitated solid was filtered off through celite, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using diethyl ether as the eluent to obtain 1.43 g of the desired product as a brown oil. The oil was used in the next step without further purification.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe precipitated solid was filtered off through celite
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6899b14ee7d24828b8c683a081fa6828
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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