Potassium Hydroxide → 5-Bromo-3,3'-bipyridine

HRID 1654641Notes

Reaction equation

HRID 1654641 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[OH-].[K+].[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(CC)CC)[CH:12]=1>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.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>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

8

Reactant 3

HCID 14797Potassium HydroxideHCID 693693,5-DibromopyridineHCID 6428513-(Diethylboryl)pyridine

Product 1

HCID 135464585-Bromo-3,3'-bipyridineYield 33%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (915 mg; 0.75 mM) was added to a solution of 3,5-dibromopyridine (4.74 g, 20 mM) in 75 mL of tetrahydrofuran. After stirring for 5 minutes tetra-n-butylammonium bromide (483 mg; 1.5 mM), finely powdered potassium hydroxide (2.52 g; 45 mM) and 3-pyridyldiethylborane (2.2 g; 15 mM) were added and the resulting reaction mixture was heated to reflux for 2 hours. The reaction mixture was cooled, diluted with 100 mL of ethyl acetate and washed with 10×25 mL of saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Solvent removal gave the crude product which was chromatographed on silica gel using ethyl acetate to give the desired product as a solid, boiling at 135°-6° C./~1 mm in 33% yield.

Workup

  1. additionwere added
  2. customthe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureto reflux for 2 hours
  5. temperatureThe reaction mixture was cooled
  6. washwashed with 10×25 mL of saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customSolvent removal
  9. customgave the crude product which
  10. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-4f358936f48d44758a3225bc73e45e68
Source dataset
uspto-grants-1995_04
Patent number
US05409920

Reaction notes

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