Iodine → HCID 173327927, compound

HRID 1941456Notes

Reaction equation

[C:1]1([C:7]2[C:8]3[NH:12][C:11]([CH:13]=[C:14]4[N:36]=[C:17]([C:18]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[C:19]5[NH:29][C:22](=[CH:23][C:24]6[CH:25]=[CH:26][C:27]=2[N:28]=6)[CH:21]=[CH:20]5)[CH:16]=[CH:15]4)=[CH:10][CH:9]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C([I:50])C=CC=1)=O.N1C=CC=CC=1>C(Cl)(Cl)Cl>[I:50][C:23]1[C:24]2[CH:25]=[CH:26][C:27]([N:28]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[NH:12][C:11]([CH:13]=[C:14]3[N:36]=[C:17]([C:18]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[C:19]4[NH:29][C:22]=1[CH:21]=[CH:20]4)[CH:16]=[CH:15]3)=[CH:10][CH:9]=2

Participants

Conditions

Temperature: 25 °C

Procedure

50 mg (0.11 mmol) of 5,15-diphenylporphyrin was dissolved in 50 ml of dry CHCl3. To the stirred solution was added 3 ml of a solution of iodine in chloroform (0.055M). Finally, a solution of 50 mg (0.12 mmol) bis(trifluoroacetoxy)iodobenzene dissolved in 25 ml of chloroform was added dropwise, followed by 200 μl of pyridine. The mixture was stirred at 25° C., in the dark, for one hour. After evaporation of the solvent in vacuo, the residue was chromatographed on silica gel, eluting with 50% 1,1-dichloromethane in hexane to give 44 mg of 10-iodo-5,15-diphenylporphyrin (70% yield). UV-Vis (CH2Cl2): λmax 422, 520, 560, 600, 660 nm; MS (EI) m/e 588(100). Annotated wavelengths for electronic absorption spectrum shown in FIG. 1:

Workup

additionwas added dropwise
customAfter evaporation of the solvent in vacuo
customthe residue was chromatographed on silica gel
washeluting with 50% 1,1-dichloromethane in hexane

Sources & evidence

ORD record: ord-a9e02320405148a581feb60905ece3af
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05703230

Reaction notes

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