4-Methoxybenzenethiol → 5-(4-Methoxyphenylthio)furan-3-carboxylic Acid

HRID 894242Notes

Reaction equation

HRID 894242 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.Br[C:11]1[O:15][CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:11]2[O:15][CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 127654-MethoxybenzenethiolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 211624815-(4-Methoxyphenylthio)furan-3-carboxylic AcidYield 42.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the procedure of Example 11, p-methoxythiophenol (4.39 g., 31.4 mmoles) and cuprous oxide (2.25 g., 15.7 mmoles) heated at 135° C. for 2 hours were reacted with 5-bromofuran-3-carboxylic acid (3 g., 15.7 mmoles) in 60 ml. of dimethylformamide, and crude product (1.67 g. ) isolated. Recrystallization from methylene chloride/hexane gave purified 5-(4-methoxphenylthio)furan-3-carboxylic acid (825 mg., m.p. 115°-117° C., m/e 250).

Sources & evidence

ORD record
ord-bb67572cc0a94d64a0227eca8f486944
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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