Acetic Acid → 5-Bromo-2-fluoropyridin-3-ol

HRID 1685411Notes

Reaction equation

HRID 1685411 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[C:5]([F:8])=[N:6][CH:7]=1.C(O)(=[O:14])C.C(OCC)(=O)C.OO>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:14])[C:5]([F:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 27832425-Bromo-2-fluoropyridine-3-boronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 201118655-Bromo-2-fluoropyridin-3-olYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 1.36 g (6.18 mM) of 5-bromo-2-fluoro-3-pyridineboronic acid in a mixture of 9.5 ml of ethanol, 2.3 ml of acetic acid and 1.3 ml of ethyl acetate is prepared. 2.2 ml of 30% hydrogen peroxide are added to the solution. The reaction mixture is stirred at a temperature of 35° C. for 3 hours and then cooled and extracted with ethyl ether. The organic phases are washed with a solution of ferrous ammonium sulfate, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The solid residue is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (9/1; v/v) as the eluent to give the desired product in the form of a white solid with a yield of 62%.

Workup

  1. customis prepared
  2. temperaturecooled
  3. extractionextracted with ethyl ether
  4. washThe organic phases are washed with a solution of ferrous ammonium sulfate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe solid residue is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (9/1; v/v) as the eluent

Sources & evidence

ORD record
ord-240c76788df04d8cb985f26908ccdd5a
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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