Hydrochloric Acid → 3(2H)-Benzofuranone, 5-bromo-2-methyl-

HRID 402916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402916
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[C:7]([O:11]C(=O)C)[C:6]=2[CH:15]=1.Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH3:10])[C:7](=[O:11])[C:6]=2[CH:15]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59192036Acetic acid 5-bromo-2-methyl-benzofuran-3-yl ester

Produkt 1

HCID 144706973(2H)-Benzofuranone, 5-bromo-2-methyl-Ausbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A suspension of acetic acid 5-bromo-2-methyl-benzofuran-3-yl ester (18.9 g, 70.4 mmol) in methanol (232 mL) and a 1 M aqueous HCl solution (44 mL) is heated under reflux (75° C.) for 7 h. After cooling to room temperature the reaction mixture is concentrated by rotary evaporation. The residue is diluted with water and extracted three times with diethyl ether. The combined organic layers are washed with water, brine, dried over Na2SO4, filtered and concentrated at reduced pressure to afford the title compound as a yellow oil (14.7 g, 64.7 mmol, 92%). MS (ES+): 227 (M(C9H779BrO2)+H)+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. concentrationis concentrated by rotary evaporation
  3. additionThe residue is diluted with water
  4. extractionextracted three times with diethyl ether
  5. washThe combined organic layers are washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-911f488407c748ac875a4d1a036bfab9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742132B2

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