1,3,5-Tribromobenzene → Ethanone, 2-bromo-1-(2,4,6-tribromophenyl)-

HRID 352563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352563
BrC1SC(Cl)=C(Cl)C=1C(=O)CCl.[Br:13][C:14]1[CH:19]=[C:18]([Br:20])[CH:17]=[C:16]([Br:21])[CH:15]=1.[Br:22][CH2:23][C:24](Br)=[O:25]>>[Br:22][CH2:23][C:24]([C:19]1[C:14]([Br:13])=[CH:15][C:16]([Br:21])=[CH:17][C:18]=1[Br:20])=[O:25]

Komponenten

4

Edukt 3

HCID 122791,3,5-TribromobenzeneHCID 61147Bromoacetyl bromideHCID 6539169Chloromethyl Thienyl Ketone deriv. 5

Produkt 1

HCID 10127285Ethanone, 2-bromo-1-(2,4,6-tribromophenyl)-Ausbeute 45 %

Versuchsvorschrift

General procedure described for compounds 1 and 2 starting from 1,3,5-tribromobenzene and bromoacetyl bromide. Purified by column chromatography column (hexane:ethyl acetate 6:1), yield 45% m.p.: 86-87° C., 1H-NMR (CDCl3): δ7.7 (s, 2H, Ar), 4.44 (s, 2H, CH2); 13C-NMR (CDCl3): δ193.4 (CO), 139.4 (C—CO), 134.5 (CH), 124.7 (C—Br), 119.4 (C—Br), 34.6 (CH2); M/z (EI): 440, 438, 436, 434, 432 (M+, 1, 3, 5, 3, 1%), 345, 343, 341, 339 (M-CH2Br, 35, 96, 100, 41%); HPLC: Column μ Bondapack C18, 5 μm, 300 A, (300×3.9 mm), Purity 98%, r.t.=3.40 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50.

Aufarbeitung

  1. customPurified by column chromatography column (hexane:ethyl acetate 6:1), yield 45% m.p.: 86-87° C., 1H-NMR (CDCl3): δ7.7 (s, 2H, Ar), 4.44 (s, 2H, CH2)
  2. customColumn μ Bondapack C18, 5 μm, 300 A, (300×3.9 mm), Purity 98%, r.t.=3.40 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50

Quellen und Nachweise

ORD-Eintrag
ord-c5e379a66aa647afbbd28357312b1007
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747057B2

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