Methanol → 5-Bromo-2-methoxypyridine

HRID 971107Notes

Reaction equation

HRID 971107 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-dccd14867cbd4cc2b7ab0b4c8cd18fe9
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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