Sodium Hydroxide → 5-Bromo-2-methoxypyridine

HRID 1884481Notes

Reaction equation

HRID 1884481 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C([O-])(=O)C.[Na+].[Br:14]Br.[OH-].[Na+]>C(O)(=O)C.O>[Br:14][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=1

Participants

7

Reactant 4

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

Product 1

HCID 27348955-Bromo-2-methoxypyridineYield 51.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 2-methoxypyridine (10.00 g, 0.09 mol) and sodium acetate (8.27 g, 0.10 mmol) in 30 mL of glacial acetic acid was added a solution of bromine in 20 mL glacial acetic acid while maintaining the reaction temperature below 50° C. After 3 hours, 100 mL of H2O was added and the resulting solution neutralized with cold 2.5 M NaOH. The suspension was extracted with ether (2×200 mL), the combined organics were dried over MgSO4, filtered and evaporated. The crude material was purified on silica gel (eluent: hexane to hexane:ethyl acetate 97:3) and distilled (34-36.5° C./0.05 mm Hg) to give 8.84 g (51.3%) of 5-bromo-2-methoxy-pyridine as a clear colorless liquid.

Workup

  1. temperaturewhile maintaining the reaction temperature below 50° C
  2. extractionThe suspension was extracted with ether (2×200 mL)
  3. dry with materialthe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was purified on silica gel (eluent: hexane to hexane:ethyl acetate 97:3)
  7. distillationdistilled (34-36.5° C./0.05 mm Hg)

Sources & evidence

ORD record
ord-61e0ebd802b9456485a3806a252406f8
Source dataset
uspto-grants-2004_07
Patent number
US06765013B2

Reaction notes

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