Ethanol → Ethyl 2-amino-3-(4-bromophenyl)propanoate

HRID 509082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 509082
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].O=S(Cl)Cl.[CH3:18][CH2:19]O>>[CH2:18]([O:4][C:3](=[O:5])[CH:2]([NH2:1])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([Br:13])=[CH:11][CH:12]=1)[CH3:19]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 856814-Bromophenylalanine

Produkt 1

HCID 4016808Ethyl 2-amino-3-(4-bromophenyl)propanoateAusbeute 72 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-amino-3-(4-bromophenyl)propanoic acid (40 g, 164 mmol) in EtOH (100 mL) was added SOCl2 (30 ml, 422 mmol) dropwise at 80° C. The mixture was stirred at 80° C. for 2 hrs. After the solvent was evaporated, the residue was extracted by EA. The combined organic layers were washed with aqueous NaCl, dried by anhydrous Na2SO4, and concentrated in vacuo to afford ethyl-2-amino-3-(4-bromophenyl)propanoate as a yellow liquid (32 g, yield: 72%).

Aufarbeitung

  1. customAfter the solvent was evaporated
  2. extractionthe residue was extracted by EA
  3. washThe combined organic layers were washed with aqueous NaCl
  4. dry with materialdried by anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-12f89228bd34420f966beb076effc6c4
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096549B2

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