Solvent-free bromination of 1,3-diketones and β-keto esters with NBS

被引:60
作者
Pravst, Igor
Zupan, Marko
Stavber, Stojan
机构
[1] Univ Ljubljana, Fac Chem & Chem Technol, SI-1000 Ljubljana, Slovenia
[2] Jozef Stefan Inst, Organ & Bioorgan Chem Lab, SI-1000 Ljubljana, Slovenia
关键词
D O I
10.1039/b608446j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Trituration of N-bromosuccinimide at room temperature with several liquid or solid 1,3-diketones and beta-keto esters resulted in high yield conversion to the monobrominated derivatives, and a work-up procedure using only water to remove succinimide was employed. The entire process uses no organic solvent and is therefore more ecologically desirable.
引用
收藏
页码:1001 / 1005
页数:5
相关论文
共 42 条
[1]  
Adams D. J., 2004, CHEM ALTERNATIVE REA
[2]  
Afonso CAM, 2005, GREEN SEPARATION PROCESSES: FUNDAMENTALS AND APPLICATIONS, P1, DOI 10.1002/3527606602
[3]  
AKHREM AA, 1968, IAN SSSR KH, P1345
[4]   NONPEPTIDE ANGIOTENSIN-II ANTAGONISTS DERIVED FROM 1H-PYRAZOLE-5-CARBOXYLATES AND 4-ARYL-1H-IMIDAZOLE-5-CARBOXYLATES [J].
ASHTON, WT ;
HUTCHINS, SM ;
GREENLEE, WJ ;
DOSS, GA ;
CHANG, RSL ;
LOTTI, VJ ;
FAUST, KA ;
CHEN, TB ;
ZINGARO, GJ ;
KIVLIGHN, SD ;
SIEGL, PKS .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (23) :3595-3605
[5]  
Boyd AJ, 1920, J CHEM SOC, V117, P1383, DOI 10.1039/ct9201701383
[6]   REGIOSPECIFIC SYNTHESIS OF UNSYMMETRICAL ALPHA-BROMOKETONES [J].
BOYD, RE ;
RASMUSSEN, CR ;
PRESS, JB .
SYNTHETIC COMMUNICATIONS, 1995, 25 (07) :1045-1051
[7]   Nonselective bromination-selective debromination strategy: Selective bromination of unsymmetrical ketones on singly activated carbon against doubly activated carbon [J].
Choi, HY ;
Chi, DY .
ORGANIC LETTERS, 2003, 5 (04) :411-414
[8]  
Clark J. H., 2008, Handbook of Green Chemistry Technology
[9]   THE CONVERSION OF ALPHA-BROMO-BETA-DICARBONYLS TO VICINAL TRICARBONYLS USING DIMETHYLDIOXIRANE AND BASE [J].
COATS, SJ ;
WASSERMAN, HH .
TETRAHEDRON LETTERS, 1995, 36 (42) :7735-7738
[10]   RATE CONSTANTS FOR HALOGEN ATOM TRANSFER FROM REPRESENTATIVE ALPHA-HALOCARBONYL COMPOUNDS TO PRIMARY ALKYL RADICALS [J].
CURRAN, DP ;
BOSCH, E ;
KAPLAN, J ;
NEWCOMB, M .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1826-1831