Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-(3,5-dichloropyridin-2-yl)ethanone

HRID 55976Notes

Reaction equation

HRID 55976 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[O:11])[CH3:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[Br-:12].[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:12][CH2:10][C:9]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=1)=[O:11]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 217121631-(3,5-Dichloropyridin-2-yl)ethanone

Product 1

HCID 534166072-Bromo-1-(3,5-dichloropyridin-2-yl)ethanoneYield 161.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5.00 g of 1-(3,5-dichloropyridin-2-yl)ethanone in 75 ml of tetrahydrofuran, 9.94 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 ethyl acetate-hexane (with a gradient of from 5:95 to 15:85) as the eluent to obtain 6.64 g of the desired product as a brown oil.

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-cd850f646e874edab909d8c8af2c313c
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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