Allyl Alcohol → [4-Amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester

HRID 2229546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229546
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([C:13](=[O:24])[NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[F:23])[CH:3]=1.[CH2:25](O)[CH:26]=[CH2:27]>OS(O)(=O)=O>[CH2:27]([O:9][C:8](=[O:10])[CH2:7][O:6][C:5]1[CH:11]=[CH:12][C:2]([NH2:1])=[CH:3][C:4]=1[C:13](=[O:24])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1[F:23])[CH:26]=[CH2:25]

Komponenten

4

Edukt 2

HCID 7858Allyl AlcoholHCID 12968791HCID 12968791, Verbindung

Produkt 1

HCID 22093473[4-Amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl esterAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidKatalysator

Versuchsvorschrift

[4-Amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy] acetic acid (0.62g, 1.56 mmol) was dissolved in allyl alcohol (15 mL, 0.1 M). This solution was treated with 7 drops of concentrated H2SO4 and stirred at room temperature for 48 h. The reaction was concentrated, redissolved in ethyl acetate, washed with H2SO, saturated aq NaCl (3×), dried over Na2SO4 and filtered. The filtrate was treated with decolorizing charcoal, boiled for 10 minutes, cooled to room temperature, filtered and concentrated. The crude solid was recrystallized from heptane and ethyl acetate to give [4-amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester as a light orange solid (0.13 g, 20%). 1H NMR (DMSO-d6, 300 MHz) δ 8.92 (br t, J=5.4 Hz, 1H), 7.49-7.80 (m, 4H); 6.84 (d, J=8.7 Hz, 1 H), 6.63 (br dd, J1=8.7 Hz, J2=2.7 Hz, 1H), 5.95-5.79 (m, 1H), 5.29 (br d, J=17.1 Hz, 1H), 5.19 (br d, J=10.5 Hz, 1 H), 4.91 (br s, 1H), 4.83 (br s, 2H), 4.61 (br d, J=5.4 Hz, 1 H).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in ethyl acetate
  3. washwashed with H2SO, saturated aq NaCl (3×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. additionThe filtrate was treated with decolorizing charcoal
  7. waitboiled for 10 minutes
  8. temperaturecooled to room temperature
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude solid was recrystallized from heptane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3315c55a2573461aafa9b5be729d6cd1
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420426B1

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