Synthesis of 1-bromo-3-methoxy-4-propoxy-5-iodobenzene - A novel efficient process for the synthesis of brominated aromatic compound

The reaction of aromatic carboxylic acid with oxalyl chloride gives rise to the corresponding acid chloride which without purification is treated with the sodium salt of mercaptopyridine oxide in the presence of 2,2-azo-bisisobutyronitrile (AIBN), radical initiator to give a brominated aromatic comp...

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Bibliographic Details
Published inChinese chemical letters Vol. 15; no. 3; pp. 288 - 291
Main Authors Shi, HX, Lin, H, Mandville, G
Format Journal Article
LanguageEnglish
Published BEIJING CHINESE CHEMICAL SOCIETY 01.03.2004
Zhejiang Key Lab. of Green-chemical Synthetic Technology, Zhejiang University of Technology, Hangzhou 310014%Department of Chemistry, Institute of Science, Zhejiang University, Hangzhou 310012%Université de Paris-Sud, ICMO, 91405 Orsay Cédex, France
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
synthesis
1-bromo-3-methoxy-4-propoxy-5-idiobenzene
PAF
radical substitution
bromination
Synthesis
bromi-nation
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Summary:The reaction of aromatic carboxylic acid with oxalyl chloride gives rise to the corresponding acid chloride which without purification is treated with the sodium salt of mercaptopyridine oxide in the presence of 2,2-azo-bisisobutyronitrile (AIBN), radical initiator to give a brominated aromatic compound. After etherification and oxidation, 5-iodovaniline was converted to trisubstituted benzene carboxylic acid which give 1-bromo-3-methoxy-4-propoxy-5-iodobenzene by this new brominating process with a yield of 74%.
ISSN:1001-8417
1878-5964