Potassium Hydroxide → 2-Benzyl-3-bromo-6-(2-ethoxyethyl)oxypyridine

HRID 1359382Notes

Reaction equation

HRID 1359382 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH3:19])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[Br:22]Br.S([O-])([O-])=O.[Na+].[Na+]>[Cl-].C([N+](CC)(CC)CC)C.[Br-].[K+]>[CH2:1]([C:8]1[C:13]([Br:22])=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH3:19])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 24408BromineHCID 24437Sodium SulfiteHCID 181822222-Benzyl-6-(2-ethoxyethyl)oxypyridine

Product 1

HCID 181821972-Benzyl-3-bromo-6-(2-ethoxyethyl)oxypyridine

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 253877Potassium BromideSolvent2×

Procedure

A mixture of 1 g of 2-benzyl-6-(2-ethoxyethyl)oxypyridine, 125 mg of tetraethylammonium chloride and 279 mg of potassium hydroxide was suspended in 5 ml of an aqueous potassium bromide solution (2.5 g of potassium bromide was dissolved in 10 ml of water). Into the suspension was added dropwise a mixture of 0.23 ml of bromine and 5 ml of the aforementioned aqueous potassium bromide solution by using a dropping funnel with stirring under ice-cooling over 10 minutes. The mixture was returned to room temperature and stirred overnight. Then, an aqueous sodium sulfite solution was added thereto, and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 5% ethyl acetate/hexane as an eluent for separation and purification, to give 1.2 g of the target compound.

Workup

  1. additionInto the suspension was added dropwise
  2. temperaturecooling over 10 minutes
  3. customwas returned to room temperature
  4. stirringstirred overnight
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was further washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed
  9. customfor separation and purification

Sources & evidence

ORD record
ord-4cd3f5dad185409c93d6a31529b5d6b1
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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