Sodium Carbonate → 5-Bromo-2-phenylpyridine

HRID 1912219Notes

Reaction equation

HRID 1912219 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]1(B(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 66827Phenylboronic AcidHCID 693532,5-Dibromopyridine

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), phenylboronic acid (4.57 g, 37.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.5 mmol) were weighed into a reaction vessel, and the reaction mixture was dissolved with stirring at 50° C. in a nitrogen stream. To this solution, a 2 M aqueous sodium carbonate solution (30 mL) was added, and the mixture was stirred at 80° C. for 6 hours. The organic layer of the obtained reaction solution was collected and washed with an aqueous sodium carbonate solution and a saturated brine. The organic layer was dried over sodium sulfate, filtered, and evaporated to dryness. This residue was purified by silica gel column chromatography (hexane/toluene). The eluate was evaporated to obtain 5-bromo-2-phenylpyridine (6.21 g, 26.5 mmol).

Workup

  1. dissolutionthe reaction mixture was dissolved
  2. stirringthe mixture was stirred at 80° C. for 6 hours
  3. customThe organic layer of the obtained reaction solution
  4. customwas collected
  5. washwashed with an aqueous sodium carbonate solution
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThis residue was purified by silica gel column chromatography (hexane/toluene)
  10. customThe eluate was evaporated

Sources & evidence

ORD record
ord-95d71f228918430ba61f46675f362bc5
Source dataset
uspto-grants-2013_12
Patent number
US08608986B2

Reaction notes

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