3,5-Dibromopyridine → 3-Bromo-5-methoxypyridine

HRID 1822150Notes

Reaction equation

HRID 1822150 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](Br)[CH:7]=1.[CH3:9][O-:10].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:10][CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 693693,5-DibromopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 8171633-Bromo-5-methoxypyridineYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3,5-dibromopyridine (32, 20 g, 84.4 mmol) in DMF (200 mL) was stirred at RT under nitrogen atmosphere and 21.3 mL of sodium methoxide (25% by wt. in methanol, 92.8 mmol) was added slowly. The reaction mixture was stirred overnight at 70° C. under N2. The reaction was cooled to RT and quenched with water (200 mL) and extracted with Et2O (2×200 mL). The combined organic extracts was washed with brine, dried (MgSO4) and concentrated in vacuo. The crude 3-bromo-5-methoxypyridine (33, 14.8 g, 93% theory) afforded a colorless oil after flash chromatography on silica gel (EtOAc:hexane 1:10).

Workup

  1. temperatureThe reaction was cooled to RT
  2. customquenched with water (200 mL)
  3. extractionextracted with Et2O (2×200 mL)
  4. washThe combined organic extracts was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46d2c3a7ff1b48578a507d8fefa27136
Source dataset
uspto-grants-2009_10
Patent number
US07608731B2

Reaction notes

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