Phosphorus tribromide → 6,6'-Dimethyl-4-ethoxy-2,2'-bipyridine

HRID 1586930Notes

Reaction equation

HRID 1586930 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][CH3:18])[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[N+:7]=1[O-].P(Br)(Br)Br>C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[CH:5]=[C:4]([O:16][CH2:17][CH3:18])[CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 149751976,6'-Dimethyl-4-ethoxy-2,2'-bipyridine-N-oxide

Product 1

HCID 149751986,6'-Dimethyl-4-ethoxy-2,2'-bipyridineYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

6,6'-Dimethyl-4-ethoxy-2,2'-bipyridine-N-oxide (21) (0.96 g, 3.93 mmoles) was dissolved in chloroform (34 ml). After addition of phosphorus tribromide (3.0 ml) the mixture was refluxed for 1.5 hours. The solution was poured on ice, some chloroform was added and the phases were separated. The chloroform phase was extracted with water. The aqueous phases were combined, made alkaline with sodium hydroxide solution, and extracted with chloroform. Evaporation of the organic phase followed by silica gel chromatography yielded pure title product. Yield: 69%

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. additionThe solution was poured on ice
  3. customthe phases were separated
  4. extractionThe chloroform phase was extracted with water
  5. extractionextracted with chloroform
  6. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-de3a327cf06b4ad4805939d7cc188dc7
Source dataset
uspto-grants-1993_06
Patent number
US05216134

Reaction notes

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