Sulfuric Acid → Methyl 5-Iodosalicylate

HRID 368296

반응식

HRID 368296 반응식
[I:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH:12](OC)(OC)OC.S(=O)(=O)(O)O>CO>[CH3:12][O:8][C:7](=[O:9])[C:6]1[C:5](=[CH:4][CH:3]=[C:2]([I:1])[CH:10]=1)[OH:11]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 83885-Iodosalicylic acidHCID 9005Trimethyl orthoformate

생성물 1

HCID 248910Methyl 5-Iodosalicylate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

5-Iodosalicylic acid (Aldrich Chemical Company, Milwaukee, Wis.) is converted to the methyl ester by reaction with methanol, trimethyl orthoformate and sulfuric acid. The 5-iodosalicylic acid methyl ester thus obtained is reacted with (trimethylsilyl)acetylene (Aldrich Chemical Company, Milwaukee, Wis.) in the presence of palladium. The trimethylsilyl group is removed and two equivalents of the resultant 5-acetylenylsalicylic acid methyl ester is reacted with 4,4'-dibromobiphenyl (Aldrich Chemical Company, Milwaukee, Wis.) in the presence of palladium as above. The resultant alkynyl analogue of Chrysamine G, 4,4'-bis(3-methoxycarbonyl-4-hydroxyphenylacetylenyl)-biphenyl is prepared by hydrolysis of the ester as described above.

출처 및 근거

ORD 기록
ord-41e292c8f77545939f90e40c8d409a74
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133259

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