Methanol → 3-Bromo-5-methoxypyridine

HRID 914756Notes

Reaction equation

HRID 914756 reaction equation
[H-].[Na+].[CH3:3][OH:4].[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10](Br)[CH:11]=1>CN(C=O)C>[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([O:4][CH3:3])[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 693693,5-Dibromopyridine

Product 1

HCID 8171633-Bromo-5-methoxypyridineYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of NaH (0.47 g, 19.6 mmol) in DMF (20 mL) was cautiously treated with methanol (0.59 g, 18.4 mmol). After 30 minutes, the mixture was treated with a solution of 3,5-dibromopyridine (4.0 g, 16.9 mmol) in DMF (5.0 mL). After stirring overnight, the reaction mixture was quenched with saturated aqueous NH4Cl and extracted with diethyl ether (200 mL). The organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 (CH2Cl2) to provide the title compound (2.24 g, 70% yield) as a yellow solid.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with diethyl ether (200 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on SiO2 (CH2Cl2)

Sources & evidence

ORD record
ord-33ea6098fa1c496ebacdc69299e54a3c
Source dataset
uspto-grants-2007_09
Patent number
US07265115B2

Reaction notes

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