Methanol → 3-Bromo-5-methoxypyridine

HRID 1642153Notes

Reaction equation

HRID 1642153 reaction equation
[CH3:1][OH:2].[Na].C[O-].[Na+].[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](Br)[CH:13]=1>CN(C=O)C>[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:2][CH3:1])[CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 693693,5-DibromopyridineHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 8171633-Bromo-5-methoxypyridineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methanol (180 mL) was treated with sodium spheres (4.7 g, 0.20 mol) portionwise, evaporated to dryness, azeotroped with toluene (100 mL), and then concentrated under reduced pressure. The sodium methoxide in dry DMF (130 mL) was treated with 3,5-dibromopyridine (32 g, 135 mmol), from Avocado Chemicals. After heating at 70° C. for 4 hours, the mixture was poured onto ice/water (300 g) and filtered. The filter cake was dried under reduced pressure to provide the title compound (15.6 g, 62% yield). MS (DCI/NH3) m/z 188/190 (M+H)+.

Workup

  1. customevaporated to dryness
  2. customazeotroped with toluene (100 mL)
  3. concentrationconcentrated under reduced pressure
  4. additionthe mixture was poured onto ice/water (300 g)
  5. filtrationfiltered
  6. customThe filter cake was dried under reduced pressure

Sources & evidence

ORD record
ord-db4d7f9ec9cf42c8931442c9b5d3c14b
Source dataset
uspto-grants-2012_02
Patent number
US08119635B2

Reaction notes

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