2-Methoxyethanol → 5-Bromo-2-(2-methoxyethoxy)pyridine

HRID 1465557Notes

Reaction equation

HRID 1465557 reaction equation
[Na].[Br:2][C:3]1[CH:4]=[CH:5][C:6]([N+]([O-])=O)=[N:7][CH:8]=1.[CH3:12][O:13][CH2:14][CH2:15][OH:16]>>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([O:16][CH2:15][CH2:14][O:13][CH3:12])=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 80192-Methoxyethanol2×HCID 8176205-Bromo-2-nitropyridineHCID 5360545Sodium

Product 1

HCID 225027175-Bromo-2-(2-methoxyethoxy)pyridineYield 86%

Procedure

To a stirred solution of sodium (591 mg, 24.6 mmol) in 2-methoxyethanol (20 mL) was added a solution of 5-bromo-2-nitropyridine (17-1, 5.00 g, 24.6 mmol) in 2-methoxyethanol (10 mL) at room temperature. The reaction mixture was stirred at reflux for 2.5 h. The solution was concentrated and the residue was diluted with CH2Cl2 and H2O. The organic layer was dried and evaporated under reduced pressure to give 5-bromo-2-(2-methoxyethoxy)pyridine (17-2, 4.9 g) in 86% yield: 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=2.6 Hz, 1 H), 7.64 (dd, J=8.7, 2.6 Hz, 1 H), 6.72 (d, J=8.7 Hz, 1 H), 4.43 (t, J=6.6 Hz, 2 H), 3.73 (t, 2H), 3.41 (s, 3 H). ESI-MS: m/z 232.0 (M+H)+.

Workup

  1. temperatureat reflux for 2.5 h
  2. concentrationThe solution was concentrated
  3. additionthe residue was diluted with CH2Cl2 and H2O
  4. customThe organic layer was dried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9d582c43d3854a84bdd1bf6b5d33216b
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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