Next Article in Journal
Inhibitory Effects of 5,6,7-Trihydroxyflavones on Tyrosinase
Previous Article in Journal
A Convenient Approach to Heterocyclic Building Blocks: Synthesis of Novel Ring Systems Containing a [5,6]Pyrano[2,3-c]pyrazol-4(1H)-one Moiety
Molecules 2007, 12(1), 74-85; doi:10.3390/12010074
Article

Simple and Regioselective Bromination of 5,6-Disubstituted-indan-1-ones with Br2 Under Acidic and Basic Conditions

 and *
Received: 21 December 2006 / Revised: 25 January 2007 / Accepted: 26 January 2007 / Published: 29 January 2007
Download PDF [138 KB, uploaded 18 June 2014]

Abstract

Bromination of 5,6-dimethoxyindan-1-one with Br2 in acetic acid at room temperature produced exclusively the corresponding 2,4-dibromo compound in 95% yield. Reaction of 5,6-dimethoxyindan-1-one with Br2 in the presence of KOH, K2CO3 or Cs2CO3 at ~0°C gave the monobrominated product 4-bromo-5,6-dimethoxyindan-3-one in 79%, 81% and 67% yield, respectively. 5,6-Dihydroxyindan-1-one was dibrominated on the aromatic ring affording 4,7-dibromo-5,6-dihydroxyindan-1-one both in acetic acid at room temperature and in the presence of KOH at ~0°C. 5,6-Difluoroindan-1-one and 1-indanone were α-monobrominated in acetic acid and α,α-dibrominated under KOH conditions at room temperature.
Keywords: 5;6-Dimethoxyindan-1-one;5;6-dihydroxyindan-1-one;regioselective aromatic bromination;α-bromination. 5; 6-Dimethoxyindan-1-one; 5; 6-dihydroxyindan-1-one; regioselective aromatic bromination; α-bromination.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

Choi, T.; Ma, E. Simple and Regioselective Bromination of 5,6-Disubstituted-indan-1-ones with Br2 Under Acidic and Basic Conditions. Molecules 2007, 12, 74-85.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert