1-Propanol → 3-Bromo-5-propoxypyridine

HRID 1642155Notes

Reaction equation

HRID 1642155 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH2:9]([OH:12])[CH2:10][CH3:11]>>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([O:12][CH2:9][CH2:10][CH3:11])[CH:7]=1

Participants

3

Reactant 2

HCID 10311-PropanolHCID 693693,5-Dibromopyridine

Product 1

HCID 226468463-Bromo-5-propoxypyridineYield 25%

Procedure

n-Propanol and 3,5-dibromopyridine were processed as described in Example 7A except that the heating time was extended to 4 hours. The reaction mixture was quenched onto ice/water, extracted with ethyl ether, and concentrated under reduced pressure. The residue was purified on silica gel (hexanes:ethyl acetate, 8:2) to provide the title compound as a colorless oil (25% yield). MS (DCI/NH3) m/z 216/218 (M+H)+.

Workup

  1. customThe reaction mixture was quenched onto ice/water
  2. extractionextracted with ethyl ether
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified on silica gel (hexanes:ethyl acetate, 8:2)

Sources & evidence

ORD record
ord-a1f44c2a751040bc85b7ebc856f08d9c
Source dataset
uspto-grants-2012_02
Patent number
US08119635B2

Reaction notes

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