Citric Acid → Bromo-acetic acid 2,4-dinitro-phenyl ester

HRID 1959571

Reaktionsgleichung

Reaktionsgleichung von HRID 1959571
[Br:1][CH2:2][C:3](Br)=[O:4].[N+:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[OH:18])([O-:8])=[O:7].N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[N+:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[O:18][C:3](=[O:4])[CH2:2][Br:1])([O-:8])=[O:7]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 1049PyridineHCID 14932,4-DinitrophenolHCID 61147Bromoacetyl bromide

Produkt 1

HCID 11278141Bromo-acetic acid 2,4-dinitro-phenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Under argon atmosphere bromo-acetyl bromide (2.67 mL, 30.66 mmol) dissolved in DCM (15 mL) was added within 15 min to a mixture of 2,4-dinitro-phenol (5.13 g, 27.88 mmol) and pyridine (2.92 mL, 36.24 mmol) in DCM (40 mL) at 0° C. After 1 h at RT, aqueous citric acid solution (10%, 30 mL) was added to the reaction mixture. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue recrystallized from diethyl ether (75 mL) to afford the title compound.

Aufarbeitung

  1. dry with materialThe organic layer was dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue recrystallized from diethyl ether (75 mL)

Quellen und Nachweise

ORD-Eintrag
ord-73231533228d4ba39352ee3bca1e76e9
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410134B2

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