Citric Acid → 3-bromo-4-methoxypyridine

HRID 1502351Notes

Reaction equation

HRID 1502351 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1F.C[O-].[Na+].CO.C(O)(=O)C[C:16](CC(O)=O)(C(O)=O)[OH:17]>>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:17][CH3:16]

Participants

5

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 27627793-bromo-4-fluoropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 6428273-bromo-4-methoxypyridineYield 40%

Procedure

3-Bromo-4-fluoropyridine (253 mg, 1.44 mmol) was suspended in a solution of sodium methoxide in methanol (3.0 mL, 4.6 M, 14 mmol) at ambient temperature, the mixture stirred for 3 days, and then poured into aqueous citric acid (1M) and extracted twice into dichloromethane. The combined organic phases were washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo to afford a yellow oil (108 mg, 40%) that was used without further purification. LCMS: M+H+=188 & 190.

Workup

  1. extractionextracted twice into dichloromethane
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7bf8516715224028b6f60ca20e949c60
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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