Chloroacetyl chloride → 2-Chloro-1-(3,4-dibromothiophen-2-yl)ethan-1-one

HRID 352559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352559
BrC1SC(Cl)=C(Cl)C=1[C:7](=[O:10])[CH2:8][Cl:9].[Br:13][C:14]1[C:18]([Br:19])=[CH:17][S:16][CH:15]=1.ClCC(Cl)=O.CCCCCC.C(OCC)(=O)C>C(#N)C.O>[Cl:9][CH2:8][C:7]([C:15]1[S:16][CH:17]=[C:18]([Br:19])[C:14]=1[Br:13])=[O:10]

Komponenten

6

Edukt 4

HCID 6577Chloroacetyl chlorideHCID 184523,4-DibromothiopheneHCID 6539169Chloromethyl Thienyl Ketone deriv. 5HCID 21226206Ethyl acetate hexane

Produkt 1

HCID 27642042-Chloro-1-(3,4-dibromothiophen-2-yl)ethan-1-oneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

General procedure described for compounds 1 and 2 starting from 3,4-dibromothiophene and chloroacetyl chloride. The product was isolated by column chromatography column (hexane:ethyl acetate 8:1). Yield 97%, m.p.: 86-8° C., 1H-NMR (CDCl3): δ7.7 (s, 1H, Ar), 4.8 (s, 2H, CH2); 13C-NMR (CDCl3): δ185.4 (CO), 140.0 (C—CO), 133.7 (CH), 120.8 (C—Br), 119.6 (C—Br), 50.1 (CH2); M/z (EI): 322, 320, 318, 316 (M+, 3, 11, 15, 7%), 271, 269, 267 (M-CH2Cl, 56, 100, 56%); HPLC: Delta Pak Column C18, 5 μm, 300 A, (150×3.9 mm), Purity 94%, r.t.=6.06 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50.

Quellen und Nachweise

ORD-Eintrag
ord-cd57abf33d5447bdb3a9f124a5b92606
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747057B2

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