Methanol → 3-Bromo-5-methoxypyridine

HRID 606788Notes

Reaction equation

HRID 606788 reaction equation
[Na].CO.CN(C)[CH:6]=[O:7].[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](Br)[CH:15]=1>O>[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([O:7][CH3:6])[CH:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 693693,5-DibromopyridineHCID 5360545Sodium

Product 1

HCID 8171633-Bromo-5-methoxypyridineYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Add sodium (0.583 g, 25 mmol) to methanol (10 mL) at 0° C. Stir the mixture at 0° C. until obtain a solution and concentrate. Add N,N-dimethylformamide (25 mL) and add 3,5-dibromopyridine (3.0 g, 12.66 mmol). Stir at 70° C. for 4 h. Cool to room temperature and add water. Extract twice with diethyl ether. Combine the organic phases, wash once with water, dry over sodium sulfate and concentrate. Purify the residue by silica gel chromatography, eluting with a gradient of 100:0 to 50:50 hexanes:ethyl acetate, to give the title compound as a solid (1.37 g, 57%).

Workup

  1. customuntil obtain a solution
  2. concentrationconcentrate
  3. stirringStir at 70° C. for 4 h
  4. temperatureCool to room temperature
  5. extractionExtract twice with diethyl ether
  6. washwash once with water
  7. dry with materialdry over sodium sulfate
  8. concentrationconcentrate
  9. customPurify the residue by silica gel chromatography
  10. washeluting with a gradient of 100:0 to 50:50 hexanes

Sources & evidence

ORD record
ord-308116b0d78f49fbab94277cf1111c4c
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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