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

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Received: 21 December 2006; in revised form: 25 January 2007 / Accepted: 26 January 2007 / Published: 29 January 2007
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.
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.
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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.

AMA 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(1):74-85.

Chicago/Turabian Style

Choi, Taeyoung; Ma, Eunsook. 2007. "Simple and Regioselective Bromination of 5,6-Disubstituted-indan-1-ones with Br2 Under Acidic and Basic Conditions." Molecules 12, no. 1: 74-85.

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