1,3,5-Tribromobenzene → HCID 19889431, compound

HRID 653620Notes

Reaction equation

HRID 653620 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.[OH-].[K+].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(CC)CC)[CH:13]=1>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Br:9][C:4]1[CH:3]=[C:2]([C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)[CH:7]=[C:6]([Br:8])[CH:5]=1

Participants

7

Reactant 3

HCID 122791,3,5-TribromobenzeneHCID 14797Potassium HydroxideHCID 6428513-(Diethylboryl)pyridine

Product 1

HCID 19889431HCID 19889431, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis-(triphenylphosphine)palladium (915 mG; 0.75 mM) was added to a stirred solution of 1,3,5-tribromobenzene (6.3 G; 20 mM) in 75 mL of anhydrous tetrahydrofuran under nitrogen at R.T. After stirring 5 mins., tetra n-butyl ammonium bromide (483 mG; 1.5 mM), followed by powdered potassium hydroxide (2.52 G, 45 mM) and 3-pyridyldiethyl borane (2.2 G; 15 mM) were added in that order. The resulting reaction mixture was heated to reflux 2 hrs., cooled, diluted with 100 mL of ethyl acetate, washed with 10×25 mL of sat'd. sodium chloride solution, and dried over anhyd. magnesium sulfate. Solvent removal, and purification on silica gel using ethyl acetate:hexane (2:3) mixture as solvent gave 1.9 G of 3-(3',5'-dibromophenyl)pyridine as a colorless oil boiling at 137°-139°/~1 mm, which slowly became a glassy solid.

Workup

  1. additionwere added in that order
  2. customThe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureto reflux 2 hrs
  5. temperature, cooled
  6. washwashed with 10×25 mL of sat'd
  7. dry with materialsodium chloride solution, and dried over anhyd
  8. customSolvent removal, and purification on silica gel

Sources & evidence

ORD record
ord-6c75dcb3886e4d2a99065d489a393532
Source dataset
uspto-grants-1992_07
Patent number
US05128335

Reaction notes

Loading…