Acetic Acid → Methyl 2-(3-bromophenyl)-2-methylpropanoate

HRID 1058586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058586
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)([CH3:5])[C:3]#N.[C:13](O)(=[O:15])C.S(=O)(=O)(O)[OH:18]>O>[CH3:13][O:15][C:3](=[O:18])[C:2]([CH3:5])([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)[CH3:1]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 105132942-(3-Bromophenyl)-2-methylpropanenitrile

Produkt 1

HCID 24777892Methyl 2-(3-bromophenyl)-2-methylpropanoateAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

2-Methyl-2-[3-bromophenyl]propionitrile (0.56 g, 2.5 mmol) was refluxed in sulfuric acid (2 ml), water (3 ml) and acetic acid (2.5 ml) overnight. The reaction mixture was poured in water, then extracted with Et2O. The combined organic extracts were dried with magnesium sulfate, filtered, concentrated, and chromatographed (silica gel, 10% EtOAc, 1% HOAc) to give the title compound as a white solid (0.2 g, 36%), which was converted to the methyl ester with diazo methane in Et2O and was used in the next reaction without further purification.

Aufarbeitung

  1. extractionextracted with Et2O
  2. dry with materialThe combined organic extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (silica gel, 10% EtOAc, 1% HOAc)

Quellen und Nachweise

ORD-Eintrag
ord-df668ddbcaab49bf9e906604c82bfd38
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518267B1

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