N-bromobutanimide → 5-Bromo-2-ethoxybenzoic acid

HRID 1037897

Reaktionsgleichung

Reaktionsgleichung von HRID 1037897
[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].[Br:13]N1C(=O)CCC1=O>C(#N)C>[Br: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 67184N-bromobutanimideHCID 672522-Ethoxybenzoic acid

Produkt 1

HCID 52099205-Bromo-2-ethoxybenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 2-ethoxybenzoic acid (3.3 g, 20.0 mmol) in 75 mL of acetonitrile at 0° C. was added N-bromosuccinimide (3.7 g, 21 mmol) in 15 mL of acetonitrile. The reaction mixture was warmed to ambient temperature and the mixture was allowed to stir for 48 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 column chromatography (SiO2, 10% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 262, 264 (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 via column chromatography (SiO2, 10% hexanes in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4b95855ec6f34f2c986a742c262e14df
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546583B2

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