Phenyltrimethylammonium bromide dibromide → HCID 118071642, compound

HRID 56005Notes

Reaction equation

HRID 56005 reaction equation
[Cl:1][C:2]1[C:3]([C:10](=[O:12])[CH3:11])=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[Br-:13].[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:13][CH2:11][C:10]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH3:9])=[CH:5][N:4]=1)=[O:12]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 838765981-(3-Chloro-5-methoxypyridin-2-yl)ethanone

Product 1

HCID 118071642HCID 118071642, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.90 g of 1-(3-chloro-5-methoxypyridin-2-yl)ethanone in 10 ml of tetrahydrofuran, 1.82 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, 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 1:9 to 3:7) as the eluent to obtain 0.57 g of the desired product as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-41bd32319c9141c3a2e89490c2af54d8
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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