New Synthetic Approach to o-Ketobenzoic Pseudo-Acid Chlorides
A new approach has been developed for the synthesis of o -ketobenzoic pseudo-acid chlorides via dehalogenation of bromo-substituted cyclic o -ketobenzoic acid esters, followed by chlorination of the resulting diesters. Homocoupling of 2-(4-bromobenzoyl)benzoic acid methyl ester gave bis-pseudo-acid...
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| Veröffentlicht in: | Russian journal of organic chemistry 2022-09, Vol.58 (9), p.1254-1259 |
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| container_title | Russian journal of organic chemistry |
| container_volume | 58 |
| creator | Yangirov, T. A. Gileva, N. G. Fatykhov, A. A. Meshcheryakova, E. S. Khalilov, L. M. Kraikin, V. A. |
| description | A new approach has been developed for the synthesis of
o
-ketobenzoic pseudo-acid chlorides via dehalogenation of bromo-substituted cyclic
o
-ketobenzoic acid esters, followed by chlorination of the resulting diesters. Homocoupling of 2-(4-bromobenzoyl)benzoic acid methyl ester gave bis-pseudo-acid chloride containing a biphenyl fragment, which could not be obtained by the traditional method involving acylation of biphenyl and subsequent chlorination of the diacid thus formed owing to deactivation of the second
para
-position in the aromatic fragment. The proposed approach solves the problem of poor solubility of polyphenylene diacids with more than three phenylene rings and makes it possible to synthesize a bis-pseudo-acid chloride with a quaterphenyl fragment. |
| doi_str_mv | 10.1134/S1070428022090093 |
| format | Article |
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o
-ketobenzoic pseudo-acid chlorides via dehalogenation of bromo-substituted cyclic
o
-ketobenzoic acid esters, followed by chlorination of the resulting diesters. Homocoupling of 2-(4-bromobenzoyl)benzoic acid methyl ester gave bis-pseudo-acid chloride containing a biphenyl fragment, which could not be obtained by the traditional method involving acylation of biphenyl and subsequent chlorination of the diacid thus formed owing to deactivation of the second
para
-position in the aromatic fragment. The proposed approach solves the problem of poor solubility of polyphenylene diacids with more than three phenylene rings and makes it possible to synthesize a bis-pseudo-acid chloride with a quaterphenyl fragment.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428022090093</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Acylation ; Benzoic acid ; Chemistry ; Chemistry and Materials Science ; Chlorides ; Chlorination ; Esters ; Organic Chemistry</subject><ispartof>Russian journal of organic chemistry, 2022-09, Vol.58 (9), p.1254-1259</ispartof><rights>Pleiades Publishing, Ltd. 2022</rights><rights>Pleiades Publishing, Ltd. 2022.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-2c51af2c8ca399e13b83a60d453768c4605cb72154a148da771afceafb778dc43</citedby><cites>FETCH-LOGICAL-c316t-2c51af2c8ca399e13b83a60d453768c4605cb72154a148da771afceafb778dc43</cites><orcidid>0000-0001-9401-8153 ; 0000-0002-7267-9716 ; 0000-0001-8826-8885 ; 0000-0003-3552-7067 ; 0000-0002-2095-9097 ; 0000-0002-7839-7402</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428022090093$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428022090093$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,778,782,27911,27912,41475,42544,51306</link.rule.ids></links><search><creatorcontrib>Yangirov, T. A.</creatorcontrib><creatorcontrib>Gileva, N. G.</creatorcontrib><creatorcontrib>Fatykhov, A. A.</creatorcontrib><creatorcontrib>Meshcheryakova, E. S.</creatorcontrib><creatorcontrib>Khalilov, L. M.</creatorcontrib><creatorcontrib>Kraikin, V. A.</creatorcontrib><title>New Synthetic Approach to o-Ketobenzoic Pseudo-Acid Chlorides</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>A new approach has been developed for the synthesis of
o
-ketobenzoic pseudo-acid chlorides via dehalogenation of bromo-substituted cyclic
o
-ketobenzoic acid esters, followed by chlorination of the resulting diesters. Homocoupling of 2-(4-bromobenzoyl)benzoic acid methyl ester gave bis-pseudo-acid chloride containing a biphenyl fragment, which could not be obtained by the traditional method involving acylation of biphenyl and subsequent chlorination of the diacid thus formed owing to deactivation of the second
para
-position in the aromatic fragment. The proposed approach solves the problem of poor solubility of polyphenylene diacids with more than three phenylene rings and makes it possible to synthesize a bis-pseudo-acid chloride with a quaterphenyl fragment.</description><subject>Acylation</subject><subject>Benzoic acid</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chlorides</subject><subject>Chlorination</subject><subject>Esters</subject><subject>Organic Chemistry</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp1kE9LAzEQxYMoWKsfwNuC5-hMJrvJHjyU4j8UFarnJZvN2i11U5MtUj-9KRU8iKcZeL_3ZniMnSKcI5K8mCEokEKDEFAClLTHRliA5kQl7ac9yXyrH7KjGBcAIFHSiF0-us9stumHuRs6m01Wq-CNnWeDzzy_d4OvXf_lk_Ic3brxfGK7JpvOlz50jYvH7KA1y-hOfuaYvV5fvUxv-cPTzd108sAtYTFwYXM0rbDaGipLh1RrMgU0MidVaCsLyG2tBObSoNSNUSrh1pm2Vko3VtKYne1y03cfaxeHauHXoU8nK6EIQcsSVaJwR9ngYwyurVahezdhUyFU25aqPy0lj9h5YmL7Nxd-k_83fQNU_2dz</recordid><startdate>20220901</startdate><enddate>20220901</enddate><creator>Yangirov, T. A.</creator><creator>Gileva, N. G.</creator><creator>Fatykhov, A. A.</creator><creator>Meshcheryakova, E. S.</creator><creator>Khalilov, L. M.</creator><creator>Kraikin, V. A.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-9401-8153</orcidid><orcidid>https://orcid.org/0000-0002-7267-9716</orcidid><orcidid>https://orcid.org/0000-0001-8826-8885</orcidid><orcidid>https://orcid.org/0000-0003-3552-7067</orcidid><orcidid>https://orcid.org/0000-0002-2095-9097</orcidid><orcidid>https://orcid.org/0000-0002-7839-7402</orcidid></search><sort><creationdate>20220901</creationdate><title>New Synthetic Approach to o-Ketobenzoic Pseudo-Acid Chlorides</title><author>Yangirov, T. A. ; Gileva, N. G. ; Fatykhov, A. A. ; Meshcheryakova, E. S. ; Khalilov, L. M. ; Kraikin, V. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-2c51af2c8ca399e13b83a60d453768c4605cb72154a148da771afceafb778dc43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Acylation</topic><topic>Benzoic acid</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chlorides</topic><topic>Chlorination</topic><topic>Esters</topic><topic>Organic Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yangirov, T. A.</creatorcontrib><creatorcontrib>Gileva, N. G.</creatorcontrib><creatorcontrib>Fatykhov, A. A.</creatorcontrib><creatorcontrib>Meshcheryakova, E. S.</creatorcontrib><creatorcontrib>Khalilov, L. M.</creatorcontrib><creatorcontrib>Kraikin, V. A.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yangirov, T. A.</au><au>Gileva, N. G.</au><au>Fatykhov, A. A.</au><au>Meshcheryakova, E. S.</au><au>Khalilov, L. M.</au><au>Kraikin, V. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Synthetic Approach to o-Ketobenzoic Pseudo-Acid Chlorides</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2022-09-01</date><risdate>2022</risdate><volume>58</volume><issue>9</issue><spage>1254</spage><epage>1259</epage><pages>1254-1259</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>A new approach has been developed for the synthesis of
o
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o
-ketobenzoic acid esters, followed by chlorination of the resulting diesters. Homocoupling of 2-(4-bromobenzoyl)benzoic acid methyl ester gave bis-pseudo-acid chloride containing a biphenyl fragment, which could not be obtained by the traditional method involving acylation of biphenyl and subsequent chlorination of the diacid thus formed owing to deactivation of the second
para
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| issn | 1070-4280 1608-3393 |
| language | eng |
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| source | Springer Nature - Complete Springer Journals |
| subjects | Acylation Benzoic acid Chemistry Chemistry and Materials Science Chlorides Chlorination Esters Organic Chemistry |
| title | New Synthetic Approach to o-Ketobenzoic Pseudo-Acid Chlorides |
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