Iodine → 2-[4-(Dimethylamino)phenyl]-6-iodo-4H-1-benzopyran-4-one

Reaction equation

[I:1]I.C([Sn](CCCC)(CCCC)[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C:13]([C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=1)=[CH:12][C:11]2=[O:27])CCC.S(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[I:1][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C:13]([C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=1)=[CH:12][C:11]2=[O:27]

Participants

Procedure

A chloroform solution of iodine (1 ml, 1 M) was added to a chloroform solution (5 ml) that contained compound 9 (30 mg, 0.054 mmol) at room temperature. The obtained mixture was reacted at room temperature for 30 minutes, and a saturated sodium bisulfite aqueous solution (5 ml) was then added thereto, so as to terminate the reaction. The chloroform layer was separated, and it was then dried over sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure, and the residue was then subjected to silica gel column chromatography using ethyl acetate/hexane (1/9) as an elution solvent, so as to obtain a product of interest, 6-iodo-4′-dimethylaminoflavone (compound 11). Yield: 10 mg (yield constant: 47.3%) 1H NMR (300 MHz, CDCl3) δ8.54 (s, 1H), 7.92 (d, J=9.0 Hz, 1H), 7.81 (d, J=9.0 Hz, 2H), 7.29 (d, J=9.0 Hz, 1H), 6.71-6.80 (m, 3H), 3.09 (s, 6H). MS m/z 392 (MH+).