Phosphorus trichloride → 4-bromo-2,2'-bipyridine

HRID 72067Notes

Reaction equation

HRID 72067 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N+:5]([O-])=[CH:6][CH:7]=1.P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 181727784-Bromo-1-oxo-2-(pyridin-2-yl)-1lambda~5~-pyridine

Product 1

HCID 120871224-bromo-2,2'-bipyridineYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred suspension of 4-bromo-2,2′-bipyridyl-N-oxide in 60 mL CHCl3, was added 12 mL PCl3, at room temperature. The mixture was refluxed for 2 h under N2 and then cooled to room temperature. The reaction mixture was poured into 100 mL ice/water. The aqueous layer was separated and saved. The CHCl3, layer was extracted three times with H2O (3×60 mL) and then discarded. The combined aqueous solution was neutralized with NaHCO3 powder to about pH 7-8. The resulting white precipitate was collected by suction filtration, washed with H2O (30 mL) and then dried under vacuum at 50° C. for 24 h. Yield: 85%.

Workup

  1. customat room temperature
  2. temperatureThe mixture was refluxed for 2 h under N2
  3. customThe aqueous layer was separated
  4. extractionThe CHCl3, layer was extracted three times with H2O (3×60 mL)
  5. filtrationThe resulting white precipitate was collected by suction filtration
  6. washwashed with H2O (30 mL)
  7. customdried under vacuum at 50° C. for 24 h

Sources & evidence

ORD record
ord-3627ce1f1bd04a75bfb9c11281d2ea87
Source dataset
uspto-grants-2014_09
Patent number
US08828204B2

Reaction notes

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