Sodium Hydroxide → 5-Bromo-2-methoxypyridine

HRID 900450Notes

Reaction equation

HRID 900450 reaction equation
[Br:1]Br.C([O-])(=O)C.[Na+].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 742012-MethoxypyridineHCID 517045Sodium Acetate

Product 1

HCID 27348955-Bromo-2-methoxypyridineYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.99 ml) was added dropwise to a stirred suspension of sodium acetate (1.59 g) and 2-methoxypyridine (1.93 ml) in acetic acid (10 ml). The reaction mixture was stirred at room temperature for 25 minutes, then at 80° C. for 2.5 h. The mixture was then allowed to cool and poured into ice-water, neutralised with 2M sodium hydroxide and extracted with ether. The combined extracts were dried (MgSO4), filtered and evaporated. The crude product was purified by column chromatography on silica gel eluting with 5% ethyl acetate in hexane to give 5-bromo-2-methoxypyridine as a colourless oil (1.75 g, 51%).

Workup

  1. waitat 80° C. for 2.5 h
  2. temperatureto cool
  3. extractionextracted with ether
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica gel eluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b252f580771d420b9ccfc9b7502a09aa
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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