Sodium Carbonate → 5-Bromo-2-phenylpyridine

HRID 2169671Notes

Reaction equation

HRID 2169671 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]1(OB(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 27628625-Bromo-2-phenylpyridineYield 88.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

2,5-dibromopyridine (7.11 g, 30 mmol), toluene (130 mL), phenylboric acid (4.57 g, 37.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.5 mmol) were weighed into a reaction container, and the reactants were dissolved, while being stirred at 50° C. under a nitrogen gas flow. A 2 M aqueous sodium carbonate solution (30 mL) was added to the solution, and the mixture was stirred at 80° C. for 6 hours. The organic layer of the obtained reaction solution was recovered, and washed with an aqueous sodium carbonate solution and a saturated saline solution. The organic layer was dried with sodium sulfate, filtered, and then distilled off. The residue was purified by silica gel column chromatography (hexane/toluene), and the solvent was distilled off to obtain 5-bromo-2-phenylpyridine (6.21 g, 26.5 mmol).

Workup

  1. dissolutionthe reactants were dissolved
  2. stirringthe mixture was stirred at 80° C. for 6 hours
  3. customThe organic layer of the obtained reaction solution
  4. customwas recovered
  5. washwashed with an aqueous sodium carbonate solution
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. filtrationfiltered
  8. distillationdistilled off
  9. customThe residue was purified by silica gel column chromatography (hexane/toluene)
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-26f8f1e216b6469ca399f6efaa052e66
Source dataset
uspto-grants-2015_06
Patent number
US09048442B2

Reaction notes

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