Sodium Carbonate → 9-(3-Bromophenyl)phenanthrene

HRID 1827603Notes

Reaction equation

HRID 1827603 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.[C:9]1(B(O)O)[C:22]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:21]2[C:22]3[C:13]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[CH:20]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 10082252Phenanthreneboronic acid

Product 1

HCID 221380359-(3-Bromophenyl)phenanthreneYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an atmosphere of argon, 3-bromoiodobenzene (7.0 g, 25 mmole), phenanthreneboronic acid (5.0 g, 23 mmole) and tetrakis-(triphenylphosphine)palladium(0) (0.5 g, 0.43 mmole, 1.7% Pd) were dissolved into toluene (100 ml). To the obtained solution, an aqueous solution of sodium carbonate (7.3 g, 69 mmole, 3 eq/35 ml) was added and the resultant solution was heated under refluxing for 10 hours and left standing for one night. The formed organic layer was separated, washed with a saturated aqueous solution of sodium chloride (50 ml) and dried with anhydrous magnesium sulfate. Then, the solvent was removed by distillation and a yellow oil was obtained. The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane, successively) and white needle crystals (6.5 g, 85%) were obtained.

Workup

  1. temperatureunder refluxing for 10 hours
  2. waitleft
  3. waitstanding for one night
  4. customThe formed organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride (50 ml)
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThen, the solvent was removed by distillation
  8. customa yellow oil was obtained
  9. customThe obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane

Sources & evidence

ORD record
ord-4408a0ae10d64655b0965289086c886b
Source dataset
uspto-grants-2006_05
Patent number
US07053255B2

Reaction notes

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