Loading…
Environmentally-Benign and Rapid Bromination of Industrially-Important Aromatics Using an Aqueous CaBr2−Br2 System as an Instant and Renewable Brominating Reagent
Selective bromination of various industrially and pharmaceutically important substituted aromatics using an aqueous CaBr2−Br2 system as an instant and renewable brominating reagent is disclosed. The direct bromination of anilines and phenols with molecular bromine in solution often results in polybr...
Saved in:
Published in: | Industrial & engineering chemistry research 2011-01, Vol.50 (2), p.705-712 |
---|---|
Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | |
---|---|
cites | |
container_end_page | 712 |
container_issue | 2 |
container_start_page | 705 |
container_title | Industrial & engineering chemistry research |
container_volume | 50 |
creator | Kumar, Lalit Mahajan, Tanu Sharma, Vivek Agarwal, Dau Dayal |
description | Selective bromination of various industrially and pharmaceutically important substituted aromatics using an aqueous CaBr2−Br2 system as an instant and renewable brominating reagent is disclosed. The direct bromination of anilines and phenols with molecular bromine in solution often results in polybromination, and when brominated in the presence of oxidants, they also get oxidized rather than undergoing substitution and, in some cases, require protection of the amino (−NH2) group. We report instantaneous, facile, and regiospecific bromination of industrially important substituted anilines, phenols, aldehydes, and anilides in excellent yields and purity under ambient conditions. The byproduct HBr waste has been utilized effectively, and the brominating reagent has been rejuvenated and reused in the subsequent brominations without any significant loss of reactivity. |
doi_str_mv | 10.1021/ie101498p |
format | article |
fullrecord | <record><control><sourceid>acs_pasca</sourceid><recordid>TN_cdi_pascalfrancis_primary_23756625</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>a108764443</sourcerecordid><originalsourceid>FETCH-LOGICAL-a167t-9d97714ee683c56e0f764cfd61cb52981b8fbff59712605dfd1ed60ac66dd8373</originalsourceid><addsrcrecordid>eNpFkUtOwzAURS0EEqUwYAeeMAzYSew4w7YqEKkSUqHj6MWfylXiBDsFdQeMWQMrYyWkBdHJe5NzP9JF6JqSW0piemc1JTTNRXeCRpTFJGIkZadoRIQQEROCnaOLEDaEEMbSdIS-5u7N-tY12vVQ17toqp1dOwxO4SV0VuGpbxvroLetw63BhVPb0Ht7gIuma30PrseTgRoYGfAqWLce9HjyutXtNuAZTH38_fE5XPy8C71uMIQ9ULhw0B6ytNPvUNX6mDe4LDWsh2KX6MxAHfTV3x-j1f38ZfYYLZ4eitlkEQHlWR_lKs8ymmrNRSIZ18RkPJVGcSorFueCVsJUxrA8ozEnTBlFteIEJOdKiSRLxujm17eDIKE2Hpy0oey8bcDvyjjJGOcxO3IgQ7lpt94NrUpKyv0E5f8EyQ-zbXzv</addsrcrecordid><sourcetype>Index Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Environmentally-Benign and Rapid Bromination of Industrially-Important Aromatics Using an Aqueous CaBr2−Br2 System as an Instant and Renewable Brominating Reagent</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><creator>Kumar, Lalit ; Mahajan, Tanu ; Sharma, Vivek ; Agarwal, Dau Dayal</creator><creatorcontrib>Kumar, Lalit ; Mahajan, Tanu ; Sharma, Vivek ; Agarwal, Dau Dayal</creatorcontrib><description>Selective bromination of various industrially and pharmaceutically important substituted aromatics using an aqueous CaBr2−Br2 system as an instant and renewable brominating reagent is disclosed. The direct bromination of anilines and phenols with molecular bromine in solution often results in polybromination, and when brominated in the presence of oxidants, they also get oxidized rather than undergoing substitution and, in some cases, require protection of the amino (−NH2) group. We report instantaneous, facile, and regiospecific bromination of industrially important substituted anilines, phenols, aldehydes, and anilides in excellent yields and purity under ambient conditions. The byproduct HBr waste has been utilized effectively, and the brominating reagent has been rejuvenated and reused in the subsequent brominations without any significant loss of reactivity.</description><identifier>ISSN: 0888-5885</identifier><identifier>EISSN: 1520-5045</identifier><identifier>DOI: 10.1021/ie101498p</identifier><identifier>CODEN: IECRED</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Applied Chemistry ; Applied sciences ; Chemical engineering ; Exact sciences and technology</subject><ispartof>Industrial & engineering chemistry research, 2011-01, Vol.50 (2), p.705-712</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23756625$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Kumar, Lalit</creatorcontrib><creatorcontrib>Mahajan, Tanu</creatorcontrib><creatorcontrib>Sharma, Vivek</creatorcontrib><creatorcontrib>Agarwal, Dau Dayal</creatorcontrib><title>Environmentally-Benign and Rapid Bromination of Industrially-Important Aromatics Using an Aqueous CaBr2−Br2 System as an Instant and Renewable Brominating Reagent</title><title>Industrial & engineering chemistry research</title><addtitle>Ind. Eng. Chem. Res</addtitle><description>Selective bromination of various industrially and pharmaceutically important substituted aromatics using an aqueous CaBr2−Br2 system as an instant and renewable brominating reagent is disclosed. The direct bromination of anilines and phenols with molecular bromine in solution often results in polybromination, and when brominated in the presence of oxidants, they also get oxidized rather than undergoing substitution and, in some cases, require protection of the amino (−NH2) group. We report instantaneous, facile, and regiospecific bromination of industrially important substituted anilines, phenols, aldehydes, and anilides in excellent yields and purity under ambient conditions. The byproduct HBr waste has been utilized effectively, and the brominating reagent has been rejuvenated and reused in the subsequent brominations without any significant loss of reactivity.</description><subject>Applied Chemistry</subject><subject>Applied sciences</subject><subject>Chemical engineering</subject><subject>Exact sciences and technology</subject><issn>0888-5885</issn><issn>1520-5045</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNpFkUtOwzAURS0EEqUwYAeeMAzYSew4w7YqEKkSUqHj6MWfylXiBDsFdQeMWQMrYyWkBdHJe5NzP9JF6JqSW0piemc1JTTNRXeCRpTFJGIkZadoRIQQEROCnaOLEDaEEMbSdIS-5u7N-tY12vVQ17toqp1dOwxO4SV0VuGpbxvroLetw63BhVPb0Ht7gIuma30PrseTgRoYGfAqWLce9HjyutXtNuAZTH38_fE5XPy8C71uMIQ9ULhw0B6ytNPvUNX6mDe4LDWsh2KX6MxAHfTV3x-j1f38ZfYYLZ4eitlkEQHlWR_lKs8ymmrNRSIZ18RkPJVGcSorFueCVsJUxrA8ozEnTBlFteIEJOdKiSRLxujm17eDIKE2Hpy0oey8bcDvyjjJGOcxO3IgQ7lpt94NrUpKyv0E5f8EyQ-zbXzv</recordid><startdate>20110119</startdate><enddate>20110119</enddate><creator>Kumar, Lalit</creator><creator>Mahajan, Tanu</creator><creator>Sharma, Vivek</creator><creator>Agarwal, Dau Dayal</creator><general>American Chemical Society</general><scope>IQODW</scope></search><sort><creationdate>20110119</creationdate><title>Environmentally-Benign and Rapid Bromination of Industrially-Important Aromatics Using an Aqueous CaBr2−Br2 System as an Instant and Renewable Brominating Reagent</title><author>Kumar, Lalit ; Mahajan, Tanu ; Sharma, Vivek ; Agarwal, Dau Dayal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a167t-9d97714ee683c56e0f764cfd61cb52981b8fbff59712605dfd1ed60ac66dd8373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Applied Chemistry</topic><topic>Applied sciences</topic><topic>Chemical engineering</topic><topic>Exact sciences and technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumar, Lalit</creatorcontrib><creatorcontrib>Mahajan, Tanu</creatorcontrib><creatorcontrib>Sharma, Vivek</creatorcontrib><creatorcontrib>Agarwal, Dau Dayal</creatorcontrib><collection>Pascal-Francis</collection><jtitle>Industrial & engineering chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumar, Lalit</au><au>Mahajan, Tanu</au><au>Sharma, Vivek</au><au>Agarwal, Dau Dayal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Environmentally-Benign and Rapid Bromination of Industrially-Important Aromatics Using an Aqueous CaBr2−Br2 System as an Instant and Renewable Brominating Reagent</atitle><jtitle>Industrial & engineering chemistry research</jtitle><addtitle>Ind. Eng. Chem. Res</addtitle><date>2011-01-19</date><risdate>2011</risdate><volume>50</volume><issue>2</issue><spage>705</spage><epage>712</epage><pages>705-712</pages><issn>0888-5885</issn><eissn>1520-5045</eissn><coden>IECRED</coden><abstract>Selective bromination of various industrially and pharmaceutically important substituted aromatics using an aqueous CaBr2−Br2 system as an instant and renewable brominating reagent is disclosed. The direct bromination of anilines and phenols with molecular bromine in solution often results in polybromination, and when brominated in the presence of oxidants, they also get oxidized rather than undergoing substitution and, in some cases, require protection of the amino (−NH2) group. We report instantaneous, facile, and regiospecific bromination of industrially important substituted anilines, phenols, aldehydes, and anilides in excellent yields and purity under ambient conditions. The byproduct HBr waste has been utilized effectively, and the brominating reagent has been rejuvenated and reused in the subsequent brominations without any significant loss of reactivity.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/ie101498p</doi><tpages>8</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0888-5885 |
ispartof | Industrial & engineering chemistry research, 2011-01, Vol.50 (2), p.705-712 |
issn | 0888-5885 1520-5045 |
language | eng |
recordid | cdi_pascalfrancis_primary_23756625 |
source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
subjects | Applied Chemistry Applied sciences Chemical engineering Exact sciences and technology |
title | Environmentally-Benign and Rapid Bromination of Industrially-Important Aromatics Using an Aqueous CaBr2−Br2 System as an Instant and Renewable Brominating Reagent |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-06T19%3A47%3A40IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_pasca&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Environmentally-Benign%20and%20Rapid%20Bromination%20of%20Industrially-Important%20Aromatics%20Using%20an%20Aqueous%20CaBr2%E2%88%92Br2%20System%20as%20an%20Instant%20and%20Renewable%20Brominating%20Reagent&rft.jtitle=Industrial%20&%20engineering%20chemistry%20research&rft.au=Kumar,%20Lalit&rft.date=2011-01-19&rft.volume=50&rft.issue=2&rft.spage=705&rft.epage=712&rft.pages=705-712&rft.issn=0888-5885&rft.eissn=1520-5045&rft.coden=IECRED&rft_id=info:doi/10.1021/ie101498p&rft_dat=%3Cacs_pasca%3Ea108764443%3C/acs_pasca%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a167t-9d97714ee683c56e0f764cfd61cb52981b8fbff59712605dfd1ed60ac66dd8373%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |