Hydrogen Peroxide → HCID 22912681, compound

HRID 1378553Notes

Reaction equation

HRID 1378553 reaction equation
I[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[Cl:9].C(=O)([O-])[O-].[Na+].[Na+].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18](B(O)O)[CH:17]=1.B(O)O.OO>C(O)C.C1C=CC=CC=1>[Cl:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[C:18]1[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 1224521,4-Dichloro-2-iodobenzeneHCID 27343783-Pyridinylboronic acid

Product 1

HCID 22912681HCID 22912681, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A 50 ml two-necked round-bottom flask is charged with 2-iodo-1,4-dichlorobenzene (5.44 g), tetrakis(triphenyl-phosphine)palladium (3 mol %, Aldrich), benzene (40 ml), and aqueous sodium carbonate solution (20 ml of 2M solution). To this vigorously stirred mixture is added 3-pyridylboronic acid (2.71 g) dissolved in a minimum amount of 95% ethanol. The reaction mixture is heated to 90°-95° C. and refluxed for 9 hours under vigorous stirring. The reaction mixture is then cooled to room temperature and the excess boronic acid is oxidized by 30% hydrogen peroxide (0.25 ml) for 1 hour. The mixture is extracted with ether, washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent is removed, and the crude product is purified by chromatography on Florisil eluting with pentane/dichloromethane (90/10) to give monomer.

Workup

  1. temperatureThe reaction mixture is heated to 90°-95° C.
  2. temperaturerefluxed for 9 hours under vigorous stirring
  3. extractionThe mixture is extracted with ether
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is removed
  7. customthe crude product is purified by chromatography on Florisil eluting with pentane/dichloromethane (90/10)
  8. customto give monomer

Sources & evidence

ORD record
ord-d7385f3524eb46a9a6a75347c8cf1a78
Source dataset
uspto-grants-1997_09
Patent number
US05668245

Reaction notes

Loading…