Water → 2-Bromo-5-propoxypyridine

HRID 1966227Notes

Reaction equation

HRID 1966227 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].I[CH2:12][CH2:13][CH3:14].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:13][CH3:14])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 665213962-Bromo-5-propoxypyridineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-5-hydroxypyridine (6 mmol) is dissolved in DMF (10 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min 1-iodopropane (1.1 eq.) is added and the reaction solution is stirred 18 hours. The reaction solution is pored into water and extracted with methyltert.-butyl ether. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. 2-Bromo-5-propoxy-pyridine is obtained as yellow oil in a yield of 87%; HPLC (method C): 1.93 min; LC-MS (method A): 1.78 min, 215.95 (M+H+).

Workup

  1. extractionextracted with methyltert.-butyl ether
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ed42e4a7a9764220bad9895d6c0abce2
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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