Water → 1-(Phenylethynyl)-4-(phenylsulfonyl)benzene

HRID 2376978

Reaktionsgleichung

Reaktionsgleichung von HRID 2376978
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[CH:2].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]1([C:2]#[C:1][C:3]2[CH:4]=[CH:5][C:6]([S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:10])=[O:11])=[CH:7][CH:8]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 11575IodobenzeneHCID 199393204-Phenylsulfonylphenylethyne

Produkt 1

HCID 210994031-(Phenylethynyl)-4-(phenylsulfonyl)benzeneAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-ethynyl-4-(phenylsulfonyl)benzene (100 mg, 0.4 mmol), iodobenzene (0.05 mL, 0.44 mmol) and triethylamine (1 mL) in toluene (1 mL) was degassed. Copper(I) iodide (3 mg, 0.004 mmol) and dichlorobis(triphenylphosphine)-palladium(II) (3 mg, 0.004 mmol) were added and the reaction stirred at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate. The organic layer was dried and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (35 mg, 28%). δH (500 MHz, d6 DMSO): 7.97 (4H, dd, J=2.6, 8.4 Hz), 7.77-7.69 (3H, m), 7.64-7.56 (4H, m), 7.43-7.41 (3H, m).

Aufarbeitung

  1. customwas degassed
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ba9a3283617640d78ac445ed19ea65b5
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468393B2

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