Toluene → 2-(4-Bromophenyl)-6-phenylnaphthalene

HRID 1662915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662915
[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(COC)OC>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:12]2[CH:11]=[CH:10][C:9]3[C:14](=[CH:15][CH:16]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:8]=3)[CH:13]=2)=[CH:23][CH:22]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 57539613(6-Phenylnaphthalen-2-yl)boronic acid

Produkt 1

HCID 575398112-(4-Bromophenyl)-6-phenylnaphthaleneAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Under an argon gas atmosphere, 21.9 g (88.3 mmol) of 6-phenylnaphthalene-2-boronic acid, 25.0 g (88.3 mmol) of 4-bromoiodobenzene, 2.00 g (1.77 mmol) of tetrakis(triphenylphosphine) palladium(0), 400 mL of toluene, 100 mL of dimethoxyethane and 132 mL of 2M sodium carbonate solution were mixed, and stirred for 15 hours while being refluxed. After the reaction in the mixture was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was cleansed by water and dried with magnesium sulfate, toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 15.3 g of 2-(4-bromophenyl)-6-phenylnaphthalene was obtained with an yield of 48%.

Aufarbeitung

  1. temperaturewhile being refluxed
  2. customAfter the reaction in the mixture
  3. filtrationfiltration
  4. dry with materialdried with magnesium sulfate, toluene
  5. distillationwas distilled away under reduced pressure
  6. customwas obtained with an yield of 48%

Quellen und Nachweise

ORD-Eintrag
ord-c577d53615314959a110599d4dea6944
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08034256B2

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