Sodium Carbonate → 3-Bromo-5-phenylpyridine

HRID 391119

Reaction equation

HRID 391119 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 693693,5-Dibromopyridine

Product 1

HCID 27629043-Bromo-5-phenylpyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 3,5-dibromopyridine (1.00 g) in toluene (10 mL) and ethanol (5 mL) was added phenylboronic acid (515 mg), sodium carbonate (1.34 g) and tetrakis (triphenylphosphine)palladium(0) (24 mg) and the reaction mixture was heated at reflux for 16 h. After cooling to room temperature, the reaction was quenched with water (30 mL) and extracted into ethylacetate (2×30 mL). The organic layers were washed with brine (40 mL), dried (MgSO4), reduced in vacuo and purified on silica to give 3-bromo-5-phenyl-pyridine as a white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. customthe reaction was quenched with water (30 mL)
  4. extractionextracted into ethylacetate (2×30 mL)
  5. washThe organic layers were washed with brine (40 mL)
  6. dry with materialdried (MgSO4)
  7. custompurified on silica

Sources & evidence

ORD record
ord-f214e01afe864228b7e59814456daeb1
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Linked notes

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