Chloroacetyl chloride → 2-Chloro-1-(2,5-dichlorothien-3-yl)ethanone

HRID 352558

Reaction equation

Br[C:2]1[S:3][C:4]([Cl:12])=[C:5](Cl)[C:6]=1[C:7](=[O:10])[CH2:8][Cl:9].[Cl:13]C1SC(Cl)=CC=1.ClCC(Cl)=O>>[Cl:9][CH2:8][C:7]([C:6]1[CH:5]=[C:4]([Cl:12])[S:3][C:2]=1[Cl:13])=[O:10]

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 185012,5-Dichlorothiophene

HCID 6539169Chloromethyl Thienyl Ketone deriv. 5

Product 1

HCID 6819572-Chloro-1-(2,5-dichlorothien-3-yl)ethanoneYield 91%

Procedure

General procedure described for compounds 1 and 2 starting from 2,5-dichlorothiophene and chloroacetyl chloride. Purified by column chromatography column (hexane:ethyl acetate 12:1), yield 91%, m.p.: 43-44° C. (ethanol), 1H-NMR (CDCl3): δ7.1 (s, 1H, CH-Aromat), 4.6 (s, 2H, CH2); 13C-NMR (CDCl3): 186.6 (CO), 136.9 (C—Cl), 136.0 (C—CO), 130.2 (C—Cl), 129.4 (CH—Ar), 50.6 (CH2); M/z (EI): 234, 232, 230, 228 (M+, 1, 6, 16, 16%), 183, 181, 179 (M-CH2Cl, 18, 79, 100%), 155, 153, 151 (M-COCH2Cl, 3, 13, 19%), 118, 116 (M-COCH2Cl2, 5, 13%); HPLC: Delta Pak Column C18, 5 μm, 300 A, (150×3.9 mm), Purity 99%, r.t.=6.16 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50.

Workup

customPurified by column chromatography column (hexane:ethyl acetate 12:1), yield 91%, m.p.: 43-44° C. (ethanol), 1H-NMR (CDCl3): δ7.1 (s, 1H, CH-Aromat), 4.6 (s, 2H, CH2)
customDelta Pak Column C18, 5 μm, 300 A, (150×3.9 mm), Purity 99%, r.t.=6.16 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50

Sources & evidence

ORD record: ord-54c64a6823ea4316b1d643fe535f6223
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747057B2

Linked notes

Loading…