Sodium Carbonate → 1~4~-Bromo-1~1~,2~1~:2~2~,3~1~-terphenyl

HRID 901750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901750
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.B(O)(O)[C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 114151-Bromo-2-iodobenzeneHCID 1512531,1'-Biphenyl-4-yl-boronic acid

Produkt 1

HCID 221380161~4~-Bromo-1~1~,2~1~:2~2~,3~1~-terphenylAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Under an atmosphere of argon, 2-bromoiodobenzene (7.9 g, 25 mmole), biphenylboronic acid (5.0 g, 25 mmole) and tetrakis(triphenyl-phosphine)palladium(0) (0.5 g, 0.43 mmole, 1.7% Pd) were dissolved into toluene (60 ml). To the obtained solution, an aqueous solution of sodium carbonate (8.0 g, 75 mmole, 3 eq/40 ml) was added. 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 (6.8 g, 88%) were obtained.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e465da2c460c491aace47da8646a683f
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361796B2

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