2-Bromo-4-nitropyridine → 2-Bromo-4-ethoxypyridine

HRID 1059931Notes

Reaction equation

HRID 1059931 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N:3]=1.[O-:11][CH2:12][CH3:13].[Na+]>C(O)C.ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([O:11][CH2:12][CH3:13])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 2430152-Bromo-4-nitropyridineHCID 2723922Sodium ethoxide

Product 1

HCID 5651602-Bromo-4-ethoxypyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-bromo-4-nitropyridine (1.0 g) in ethanol (5 ml) was added a solution of sodium ethoxide in ethanol (20%, 2 ml), and the resultant mixture was stirred at 85° C. for 1.5 hours. After cooling, the mixture was diluted with dichloromethane and washed with water and brine. The separated organic layer was dried over sodium sulfate and evaporated under reduced pressure to give 2-bromo-4-ethoxypyridine (927 mg).

Workup

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialThe separated organic layer was dried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2396fc09793a41e1ac02dc47d8681d1b
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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