Methanol → 5-Bromo-2-methoxypyridine

HRID 1839158Notes

Reaction equation

HRID 1839158 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.CO.C[C:12](C)([O-:14])C.[K+]>CN(C)C=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:14][CH3:12])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 693532,5-DibromopyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 27348955-Bromo-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5-dibromopyridine (6.95 g, 29 mmol) in N,N-dimethylformamide (5 ml) was added methanol (3.56 ml) and 1M potassium tert-butoxide (32.3 ml) and the resulting mixture was stirred at room temperature for 18 hours. The resulting slurry was quenched with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with a 1:9 mixture of ether and hexane to afford the 5-Bromo-2-methoxypyridine compound as an oil.

Workup

  1. customThe resulting slurry was quenched with saturated aqueous ammonium chloride solution
  2. custompartitioned between ethyl acetate and water
  3. customThe crude product from the organic phase was chromatographed on silica gel eluting with a 1:9 mixture of ether and hexane

Sources & evidence

ORD record
ord-d15a22c605134c3681922956b2c7bebc
Source dataset
uspto-grants-2004_01
Patent number
US06677351B2

Reaction notes

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