2,6-Dibromopyridine → HCID 54427508, compound

HRID 1636178Notes

Reaction equation

HRID 1636178 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:11])[O:8][C@H:7]([CH2:9][OH:10])[CH2:6][O:5]1.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[N:14]=1>C1(C)C=CC=CC=1.O>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:10][CH2:9][C@@H:7]2[CH2:6][O:5][C:4]([CH3:11])([CH3:3])[O:8]2)[N:14]=1

Participants

6

Reactant 3

HCID 122742,6-DibromopyridineHCID 24758Sodium hydrideHCID 736056(R)-Solketal

Product 1

HCID 54427508HCID 54427508, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Sodium hydride (1.62 g, 60% dispersion in mineral oil, 40.5 mmol) was added portionwise to an ice-cooled solution of (R)-(−)-1,2-O-isopropylideneglycerol (4.86 g, 36.8 mmol) in toluene (100 ml), and once addition was complete, the solution was allowed to warm to room temperature and stirred for 30 minutes. 2,6-Dibromopyridine (8.72 g, 36.8 mmol) was added, and the reaction heated under reflux for 5 hours. The cooled mixture was diluted with water, the layers separated, and the aqueous phase extracted with ether. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo to afford the title compound as a yellow oil (quantitative).

Workup

  1. temperaturecooled
  2. temperaturethe reaction heated
  3. temperatureunder reflux for 5 hours
  4. customthe layers separated
  5. extractionthe aqueous phase extracted with ether
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-2a7cbe8558cc49258c4abfaab9a69102
Source dataset
uspto-grants-2003_01
Patent number
US06511993B1

Reaction notes

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