Toluene → Ethyl 2-(4-fluorophenyl)-5-hydroxybenzofuran-3-carboxylate

HRID 705334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705334
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[C:23]1(=O)[CH:28]=[CH:27][C:26](=[O:29])[CH:25]=[CH:24]1>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:15][C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=3[C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 4650QuinoneHCID 2758844Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Produkt 1

HCID 56604952Ethyl 2-(4-fluorophenyl)-5-hydroxybenzofuran-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The material prepared in Example 1A (250 g, 1.19 mole) was combined with zinc chloride (243.5 g, 1.784 mole) and toluene (3.75 L). The reaction mixture was heated to reflux under a nitrogen atmosphere. Benzoquinone (167 g, 1.546 mole) in tetrahydrofuran (500 mL) was added dropwise to the reaction, and upon completion of the addition, the reaction mixture was heated at reflux for 6 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was concentrated in vacuo to a brown solid. The solid was recrystallized from acetonitrile yielding the title compound as a brown solid (125 g, 35%). MS m/z 301 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere
  3. additionupon completion of the addition
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 6 hours
  6. customThe reaction mixture was quenched with water
  7. extractionextracted with ethyl acetate
  8. concentrationThe organic layer was concentrated in vacuo to a brown solid
  9. customThe solid was recrystallized from acetonitrile yielding the title compound as a brown solid (125 g, 35%)

Quellen und Nachweise

ORD-Eintrag
ord-4b9b4ec8eb144e82acbc16f296163900
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173887B2

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