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Molecules 2007, 12(1), 74-85; doi:10.3390/12010074

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

College of Pharmacy, Catholic University of Daegu, Hayang, 712-702, Korea
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Author to whom correspondence should be addressed.
Received: 21 December 2006 / Revised: 25 January 2007 / Accepted: 26 January 2007 / Published: 29 January 2007
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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 (CC BY 3.0).

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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.

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