1-Butanol → 3-Bromo-2-butoxy-5-methyl-pyridine

HRID 1766442Notes

Reaction equation

HRID 1766442 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][CH3:6].[Br:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:8][C:9]1[C:10]([O:7][CH2:3][CH2:4][CH2:5][CH3:6])=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 24758Sodium hydrideHCID 2854373-Bromo-2-chloro-5-methylpyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 211096993-Bromo-2-butoxy-5-methyl-pyridineYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride dispersion in oil (55–65%, 1.16 g) was added in portions to a well stirred solution of 1-butanol (2.4 mL, 27 mmol) in DMF (50 mL). After stirring the mixture for 1 h at room temperature 3-bromo-2-chloro-5-methyl-pyridine (5.0 g, 24 mmol) was added and stirring continued for 18 h at room temperature and for 4 h at 70° C. The cooled mixture was poured into saturated sodium bicarbonate solution and extracted with diethyl ether. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography on silica (n-heptane/ethyl acetate 8:1) to yield 4.2 g of the title compound as a light red oil, MS (EI) 243.1, 245.1 (M)+.

Workup

  1. additionwas added
  2. extractionextracted with diethyl ether
  3. dry with materialdried with Na2SO4
  4. customthe solvent was evaporated
  5. customThe residue was purified by column chromatography on silica (n-heptane/ethyl acetate 8:1)

Sources & evidence

ORD record
ord-1b999166493a4258b4cc52b5640d9626
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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