Simple and Regioselective Bromination of 5,6-Disubstituted-indan-1-ones with Br2 Under Acidic and Basic Conditions 英文参考文献.docVIP

Molecules 2007, 12, 74-85 molecules ISSN 1420-3049 Full Paper Simple and Regioselective Bromination of 5,6-Disubstituted- indan-1-ones with Br2 Under Acidic and Basic Conditions Taeyoung Choi and Eunsook Ma * College of Pharmacy, Catholic University of Daegu, Hayang, 712-702, Korea, Tel. 82-053-850-3621, Fax. 82-053-850-3602. * Author to whom correspondence should be addressed; E-mail: masook@cu.ac.kr Received: 21 December 2006; in revised form: 25 January 2007 / Accepted: 26 January 2007 / Published: 29 January 2007 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. Introduction Bromoaromatics are widely used as intermediates in the manufacture of pharmaceuticals, agrochemicals and specialty chemical products [1]. Recently, bromoarenes have assumed increasing importance in organic synthesis as useful reagents for functionalization through carbon-carbon bond formation of diarenes, ethylenic, or acetylenic condensation via metal catalyzed cross coupling reactions such as the Suzuki, Negishi, and Sonogashira reactions [2]. Various reagents and reaction  Molecules 2007, 12 75 conditions have been developed and reported for the brom