Chloroacetyl chloride → 1-(5-Acetyl-thiophen-2-yl)-2-chloro-ethanone

HRID 352561Notes

Reaction equation

BrC1SC(Cl)=C(Cl)C=1C(=O)CCl.[C:13]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=[O:15])[CH3:14].[Cl:21][CH2:22][C:23](Cl)=[O:24]>>[C:13]([C:16]1[S:17][C:18]([C:23](=[O:24])[CH2:22][Cl:21])=[CH:19][CH:20]=1)(=[O:15])[CH3:14]

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 69202-Acetylthiophene

HCID 6539169Chloromethyl Thienyl Ketone deriv. 5

Product 1

HCID 41657081-(5-Acetyl-thiophen-2-yl)-2-chloro-ethanoneYield 25%

Procedure

General procedure described for compounds 1 and 2 starting from 2-acetylthiophene and chloroacetyl chloride. Purified by column chromatography column (hexane:ethyl acetate 3:1), yield 25%, m.p.: 94-95° C., 1H-NMR (CDCl3): δ8.3 (d, J=4.2 Hz, 1H, Ar), 8.1 (d, J=4.2 Hz, 1H, Ar), 4.55 (s, 2H, CH2), 2.6 (s, 3H, CH3); 13C-NMR (CDCl3). δ193.0 (CO), 187.8 (CO), 148.3 (C—CO), 142.0 (CH), 141.7 (C—CO), 133.7 (CH), 48.3 (CH2), 29.2 (CH3); M/z (EI): 204, 202 (M +, 4, 10%), 153 (M-CH2Cl, 100%); HPLC: Column μ Bondapack C18, 5 μm, 300 A, (300×3.9 mm), Purity 98%, r.t.=3.50 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50.

Workup

customPurified by column chromatography column (hexane:ethyl acetate 3:1), yield 25%, m.p.: 94-95° C., 1H-NMR (CDCl3): δ8.3 (d, J=4.2 Hz, 1H, Ar), 8.1 (d, J=4.2 Hz, 1H, Ar), 4.55 (s, 2H, CH2), 2.6 (s, 3H, CH3)
customColumn μ Bondapack C18, 5 μm, 300 A, (300×3.9 mm), Purity 98%, r.t.=3.50 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50

Sources & evidence

ORD record: ord-1ebba97bc0534d7e81d9088cc6554563
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747057B2

Reaction notes

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