Iodine → HCID 53681800, compound

HRID 2418708Notes

Reaction equation

HRID 2418708 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)[CH3:2].[I:17]I>C(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][C:8]1[C:13]([I:17])=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)[CH3:2]

Participants

5

Reactant 2

HCID 807IodineHCID 15322109HCID 15322109, compound

Product 1

HCID 53681800HCID 53681800, compound

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

4(3-methoxyphenyl)butyric acid ethyl ester is iodinated with iodine and silver trifluoroacetate in methylene chloride to give 4(6-iodo-3-methoxyphenyl)butyric acid ethyl ester. This compound is heated at 80° C. with methylthiolithium in dimethylformamide in the presence of CuO. The resulting product is hydrolyzed with NaOH to give 4(6-methylthio-3-methoxyphenyl)butyric acid, which is cyclyzed with polyphosphoric acid to obtain 5-methylthio-8-methoxy-1,2,3,4-tetrahydro-1-naphthalenone.

Sources & evidence

ORD record
ord-27fc026269314bc09e7a35095b5a4c17
Source dataset
uspto-grants-1984_09
Patent number
US04473586

Reaction notes

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