Chlorosuccinimide → 5-Chloro-2-ethoxybenzoic acid

HRID 78477

Reaktionsgleichung

Reaktionsgleichung von HRID 78477
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 672522-Ethoxybenzoic acid

Produkt 1

HCID 50985705-Chloro-2-ethoxybenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 2-ethoxybenzoic acid (4.4 g, 26.6 mmol) in 80 mL of acetonitrile at 0° C. was added N-chlorosuccinimide (3.7 g, 28 mmol) in 20 mL of acetonitrile dropwise over 30 minutes. The reaction mixture was warmed to ambient temperature and the mixture was allowed to stir for 70 hours. The mixture was quenched with 20 mL of H2O and the layers were separated. The aqueous layer was extracted with three 15 mL portions of CH2Cl2 and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via recrystallization with ether and hexanes afforded the title compound. MS (DCI/NH3) m/z 201 (M+H)+, 218 (M+NH4)+.

Aufarbeitung

  1. customThe mixture was quenched with 20 mL of H2O
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with three 15 mL portions of CH2Cl2
  4. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. customvia recrystallization with ether and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-029cf09010894e74b3ccb96a99e26c5d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

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