2-Bromo-3-pyridinol → 2-Phenyl-3-pyridinol

HRID 1244032Notes

Reaction equation

HRID 1244032 reaction equation
Br[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[C:9]1([C:2]2[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 230702-Bromo-3-pyridinolHCID 66827Phenylboronic Acid

Product 1

HCID 187052-Phenyl-3-pyridinolYield 42.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a 1 liter round bottom flask equipped with a nitrogen inlet and a condenser was introduced 25 gm. (143.68 mmol) 2-bromo-3-hydroxypyridine, 19.27 gm. (156 mmol) phenylboronic acid, 5 gm (4.31 mmol) tetrakistriphenylphosphine palladium (0). The contents were dissolved in 300 ml of benzene and 100 ml of 2M aqueous sodium carbonate solution. The reaction mixture was heated under reflux for a period of 18 hours. The mixture was allowed to cool to room temperature and extracted with ethyl acetate (4×100 ml). The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was taken up in chloroform followed by treatment with ether to afford a solid precipitate. Upon filtration there was obtained 10.4 gm (42%) of 2-phenyl-3-hydroxypyridine. 1H NMR (CDCl3, 400 MHz) δ 8.22 (d, 1H), 7.71 (d, 2H), 7.51–7.40 (m, 2H), 7.22 (d, 2H), 7.15 (m, 1H) ppm. Mass spectrum APCI m/z 172 (p+1).

Workup

  1. customTo a 1 liter round bottom flask equipped with a nitrogen inlet and a condenser
  2. additionwas introduced 25 gm
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for a period of 18 hours
  5. extractionextracted with ethyl acetate (4×100 ml)
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a solid precipitate
  9. filtrationUpon filtration there

Sources & evidence

ORD record
ord-77c009fbd50c4a3291c58874f0183ec9
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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