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1-Hexanol → 5-Bromo-2-hexyloxypyridine

HRID 376752
Notes
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Reaction equation

HRID 376752 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].Br[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=1>CN(C=O)C>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[N:12][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81031-HexanolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 221180785-Bromo-2-hexyloxypyridineYield 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
80 °C

Procedure

A solution of 300 mmol of 1-hexanol in 100 ml of DMF is added dropwise at 50° C. under a protective gas to a suspension of 300 mmol of sodium hydride (80 percent in mineral oil) in 100 ml of dry DMF. The mixture is stirred at 80° C. for 1 hour, and a solution of 200 mmol of 2,5-dibromopyridine in 150 ml of warm DMF is subsequently slowly added dropwise. The mixture is then stirred at 80° C. for 3-4 hours. For hydrolysis, the cooled reaction mixture is introduced into 1 l of ice/water, the mixture is extracted a number of times with dichloromethane, and the combined organic extracts are washed with sat. sodium chloride solution and dried using sodium sulfate. After the solvent has been removed in vacuo, the residue is chromatographed on silica gel 60 using dichloromethane as eluent, giving 52 g (quant. yield) of a viscous liquid.

Workup

  1. stirringThe mixture is then stirred at 80° C. for 3-4 hours
  2. customFor hydrolysis
  3. customthe cooled reaction mixture
  4. extractionthe mixture is extracted a number of times with dichloromethane
  5. washthe combined organic extracts are washed with sat. sodium chloride solution
  6. customdried
  7. customAfter the solvent has been removed in vacuo
  8. customthe residue is chromatographed on silica gel 60 using dichloromethane as eluent

Sources & evidence

ORD record
ord-a0fdd0cd01bb4e1fbdac1dd9d4e7776b
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06022492

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes