Ammonium nitrate → 4,4'-Dibromobenzil

HRID 1739361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739361
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[OH:11])=[O:9])=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[NH4+]>C(O)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=2)=[O:11])=[O:9])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 22985Ammonium nitrateHCID 39382431,2-Bis(4-bromophenyl)-2-hydroxyethanone

Produkt 1

HCID 964304,4'-DibromobenzilAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 4,4'-dibromobenzoin (20.2 g, 0.055 mol), ammonium nitrate (4.6 g, 0.0575 mol) and copper(II) acetate (0.100 g, 0.0005 mol) in 80 percent aqueous acetic acid (200 mL) is heated at reflux for three hours. The reaction mixture is cooled to room temperature and the product which crystallizes out is filtered off, washed with ethanol and dried, giving 13.0 g (64 percent) of product as a light yellow solid, mp 226° C. to 228° C. 1H NMR (CDCl3) δ 7.83 (d, J=8.5 Hz, 4H), 7.66 (d, J=8.5 Hz, 4H); 13C NMR (CDCl3) δ 192.25, 132.44, 131.45, 131.22, 130.7.

Aufarbeitung

  1. temperatureat reflux for three hours
  2. customthe product which crystallizes out
  3. filtrationis filtered off
  4. washwashed with ethanol
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4a898eebc49f413ca412af05344043c3
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965679

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