Sodium Carbonate → 5-Bromo-2-phenylpyridine

HRID 2047608Notes

Reaction equation

HRID 2047608 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 and placed into a reactor. A reactant was dissolved under a nitrogen stream while stirring at 50° C. To this, a 2 M sodium carbonate aqueous solution (30 mL) was added, and stirring was performed at 80° C. for 6 hours. An organic layer of the obtained reaction solution was collected, and washed with a sodium carbonate aqueous solution and a saturated brine. The organic layer was dried with sodium sulfate, filtered, and then distilled off. This residue was purified using silica gel column chromatography (hexane/toluene) to distill off the solvent, and 5-bromo-2-phenylpyridine (6.21 g, 26.5 mmol) was obtained.

Workup

  1. customplaced into a reactor
  2. dissolutionA reactant was dissolved under a nitrogen stream
  3. stirringstirring
  4. customAn organic layer of the obtained reaction solution
  5. customwas collected
  6. washwashed with a sodium carbonate aqueous solution
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. distillationdistilled off
  10. customThis residue was purified
  11. distillationto distill off the solvent

Sources & evidence

ORD record
ord-64b1ffe2181044aeb88b92cda561ffec
Source dataset
uspto-grants-2013_11
Patent number
US08592544B2

Reaction notes

Loading…