2,6-Dibromopyridine → HCID 22288643, compound

HRID 968306Notes

Reaction equation

HRID 968306 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18](Br)[N:17]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:15][C:16]1[N:17]=[C:18]([O:3][CH2:4][CH2:5][O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=2)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 122742,6-DibromopyridineHCID 24758Sodium hydrideHCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-

Product 1

HCID 22288643HCID 22288643, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a 60% suspension of sodium hydride (0.22 g) in DMF (30 mL), 4-(2-hydroxyethoxy)benzaldehyde (1.00 g) was added at 0° C., and the suspension was stirred for 30 minutes. Subsequently, 2,6-dibromopyridine (2.14 g) and tetrabutylammonium iodide (0.022 g) were sequentially added to the mixture at 0° C., and the resultant mixture was stirred at room temperature for two hours. After completion of reaction, the reaction mixture was poured into an ice-water mixture, and the thus-formed organic matter was separated through extraction by use of ethyl acetate, followed by washing with water. The washed product was dried over magnesium sulfate, and the residual solvent was removed through distillation under reduced pressure. The thus-yielded residue was purified by means of a silica gel column, to thereby yield 1.50 g of the title compound as colorless crystals (yield 77.3%).

Workup

  1. customAfter completion of reaction
  2. customthe thus-formed organic matter was separated through extraction by use of ethyl acetate
  3. washby washing with water
  4. dry with materialThe washed product was dried over magnesium sulfate
  5. customthe residual solvent was removed through distillation under reduced pressure
  6. customThe thus-yielded residue was purified by means of a silica gel column

Sources & evidence

ORD record
ord-bf30a5d4dcf34124acd476cee4dae779
Source dataset
uspto-grants-2005_10
Patent number
US06958353B2

Reaction notes

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