Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:7](=[O:9])[CH3:8])[S:5][CH:6]=1.FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C([I:21])C=CC=1)=O.II>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[I:21][C:6]1[S:5][C:4]([C:7](=[O:9])[CH3:8])=[CH:3][C:2]=1[CH3:1]Participants
Procedure
Commercially available 1-(4-Methyl-thiophen-2-yl)-ethanone (2.0 g, 14.2 mmol) was combined with bis(trifluoroacetoxy)iodobenzene (6.3 g, 14.2 mmol) and iodine (3.6 g, 14.2 mmol) in CCl4 (30 ml). The purple suspension was stirred for 2 h upon which time the reaction was judged to be complete by HPLC. The reaction was diluted with CH2Cl2 and washed with Na2S2O3 (aq, sat.) until the purple color dissipated. The organics were washed with H2O and brine. The aqueous layers were extracted once with CH2Cl2 and the combined organics were dried (Na2SO4), filtered and concentrated by rotary evaporation to give a yellow residue which was purified by flash column chromatography (hexanes:ethyl acetate gradient 2–50% ethyl acetate) to give 1-(5-Iodo-4-methyl-thiophen-2-yl)-ethanone (2.5 g, 66%) as a solid; MS (ESI) m/z 266.9 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ 7.65 (s, 1H), 2.47 (s, 3H), 2.19 (s, 3H).
Workup
- washwashed with Na2S2O3 (aq, sat.) until the purple color
- washThe organics were washed with H2O and brine
- extractionThe aqueous layers were extracted once with CH2Cl2
- dry with materialthe combined organics were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
- customto give a yellow residue which
- customwas purified by flash column chromatography (hexanes:ethyl acetate gradient 2–50% ethyl acetate)
Sources & evidence
- ORD record
- ord-dc3083b835fa49c48a6b93a87bff5204
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07119205B2
Linked notes
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