Ethanol → 5-Bromo-2-ethoxypyridine

HRID 993249Notes

Reaction equation

HRID 993249 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].CCO.Br[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1>O>[Br:15][C:12]1[CH:11]=[N:10][C:9]([O:3][CH2:2][CH3:1])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 693532,5-DibromopyridineHCID 2723922Sodium ethoxide

Product 1

HCID 8172375-Bromo-2-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of NaOEt in EtOH (21%; 157 mL, 422 mmol) was added to 2,5-dibromopyridine (4-1) (20 g; 84.4 mmol) and the mixture heated to 80° C. for 16 hours. After cooling, the mixture was poured into water, extracted twice with EtOAc, washed with water then brine, dried (MgSO4) and concentrated under reduced pressure to give crude product 4-2 as a solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with EtOAc
  3. washwashed with water
  4. dry with materialbrine, dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0075f4ff57d4c2b8436ce4d76c73e39
Source dataset
uspto-grants-2002_10
Patent number
US06472403B2

Reaction notes

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