Benzene, 1-chloro-4-ethynyl- → {2-Chloro-4-[3-(4-chloro-phenylethynyl)-5-hydroxy-phenylsulfanyl]-phenoxy}-acetic Acid Ethyl Ester

HRID 1513106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513106
[CH2:1]([O:3][C:4](=[O:6])[CH3:5])[CH3:2].Br[C:8]1[CH:9]=[C:10]([S:15][C:16]2[CH:26]=[CH:25][C:19]([O:20]CC(O)=O)=[C:18]([Cl:27])[CH:17]=2)[CH:11]=[C:12]([OH:14])[CH:13]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[CH:36])=[CH:31][CH:30]=1>C(N(CC)CC)C.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu](I)I>[CH2:1]([O:3][C:4](=[O:6])[CH2:5][O:20][C:19]1[CH:25]=[CH:26][C:16]([S:15][C:10]2[CH:11]=[C:12]([OH:14])[CH:13]=[C:8]([C:36]#[C:35][C:32]3[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=3)[CH:9]=2)=[CH:17][C:18]=1[Cl:27])[CH3:2]

Komponenten

7

Edukt 2

HCID 70118Benzene, 1-chloro-4-ethynyl-HCID 67024266[4-(3-Bromo-5-hydroxy-phenylsulfanyl)-2-chloro-phenoxy]-acetic Acid Ethyl Acetate

Produkt 1

HCID 57791919{2-Chloro-4-[3-(4-chloro-phenylethynyl)-5-hydroxy-phenylsulfanyl]-phenoxy}-acetic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

[4-(3-Bromo-5-hydroxy-phenylsulfanyl)-2-chloro-phenoxy]-acetic acid ethyl acetate (1.1 g; 2.63 mmol), 4-chlorophenylacetylene (1.08 g; 7.9 mmol), bis(triphenylphosphine)-palladium (II) chloride (0.15 g; 0.21 mmol) and copper iodide (0.03 g; 0.16 mmol) were dissolved in a mixture of triethylamine (5 mL) and DMF (5 mL) under an atmosphere of nitrogen. The reaction mixture was reacted in a microwave oven at 100° C. for 1 h. The reaction mixture was evaporated to dryness and portioned between 5% aqueous citric acid and ethyl acetate. The organic phase was dried and evaporated to dryness. The crude product was purified by flash chromatography (ethyl acetate:heptane 1:3). Yield: 1.1 g. HPLC-MS: m/z: 473.3 (M+); Rt: 2.76 min.

Aufarbeitung

  1. customThe reaction mixture was reacted in a microwave oven at 100° C. for 1 h
  2. customThe reaction mixture was evaporated to dryness
  3. customThe organic phase was dried
  4. customevaporated to dryness
  5. customThe crude product was purified by flash chromatography (ethyl acetate:heptane 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-3129ef06903c45f2b1c6ee01f62225e2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217086B2

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