Bromination of 3-substituted benzo[b]thiophenes: access to Raloxifen intermediate

被引：9
作者：
Liger, Francois [1 ]
Pellet-Rostaing, Stephane [1 ]
Popowycz, Florence [1 ]
Lemaire, Marc [1 ]
机构：
[1] Univ Lyon 1, Equipe Catalyse Synth Environm, Inst Chim & Biochim Mol & Supramol, UMR CNRS 5246, F-69622 Villeurbanne, France
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 29期
关键词：
Benzo[b]thiophene; Bromination; Electrophilic aromatic substitution; Raloxifen; PICTET-SPENGLER REACTION; HECK; DERIVATIVES; ESTERS;
D O I：
10.1016/j.tetlet.2011.05.043
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical route to prepare halogeno-derivatives is described, starting from easily available 3-cyano-benzo[b]thiophene. Main efforts have been devoted to the optimization of the experimental procedures (solvent, bromination) to promote selectivity. Synthetic studies investigate the potential access to an advanced intermediate of Raloxifen. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3736 / 3739
页数：4
相关论文
共 20 条
[1]   ELECTROPHILIC AROMATIC REACTIVITIES VIA PYROLYSIS OF 1-ARYLETHYL ESTERS .17. REACTIVITY OF 2-POSITIONS AND 3-POSITIONS OF BENZO[B]FURAN AND OF ALL POSITIONS IN BENZO[B]THIOPHEN [J].
AMIN, HB ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (10) :1053-1058
[2]  
CAGNIANT P, 1966, B SOC CHIM FR, P3055
[3]   Benzo[b]thiophene as a template for substituted quinolines and tetrahydroquinolines [J].
Chabert, JFD ;
Chatelain, G ;
Pellet-Rostaing, S ;
Bouchu, D ;
Lemaire, M .
TETRAHEDRON LETTERS, 2006, 47 (06) :1015-1018
[4]   An efficient phosphine-free palladium coupling for the synthesis of new 2-arylbenzo[b]thiophenes [J].
Chabert, JFD ;
Joucla, L ;
David, E ;
Lemaire, M .
TETRAHEDRON, 2004, 60 (14) :3221-3230
[5]  
Chabert JFD, 2002, TETRAHEDRON LETT, V43, P1829
[6]  
CROSS PE, 1989, HETEROCYCLES, V23, P2391
[7]   Efficient access to 2-aryl-3-substituted benzo[b]thiophenes [J].
David, E ;
Perrin, J ;
Pellet-Rostaing, S ;
Chabert, JFD ;
Lemaire, M .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3569-3573
[8]   Synthesis of fluorescent rhodamine dyes using an extension of the Heck reaction [J].
David, Emilie ;
Lejeune, Johan ;
Pellet-Rostaing, Stephane ;
Schulz, RIrgen ;
Lemaire, Marc ;
Chauvin, Jerome ;
Deronzier, Alain .
TETRAHEDRON LETTERS, 2008, 49 (11) :1860-1864
[9]   Heck-like coupling and Pictet-Spengler reaction for the synthesis of benzothieno[3,2-c]quinolines [J].
David, Emilie ;
Pellet-Rostaing, Ephane ;
Lemaire, Marc .
TETRAHEDRON, 2007, 63 (36) :8999-9006
[10]   Synthesis of benz[c]benzothiopheno[2,3-e]azepines via Heck-type coupling and Pictet-Spengler reaction [J].
David, Emilie ;
Rangheard, Claudine ;
Pellet-Rostaing, Stephane ;
Lemaire, Marc .
SYNLETT, 2006, (13) :2016-2020
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