Electric Literature of 1073-39-8, These common heterocyclic compound, 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Step 2 N-(bicyclo[4.2.0]octa-1(6),2,4-trienyl-3-yl)-N’-(tert-butoxycarbonyl-hydrazino)-tert-butyl-carbonate; 3-Bromo-bicyclo[4.2.0]octa-1(6),2,4-triene 5b (13.5 g,73.8 mmol) was dissolved in 100 mL of dry tetrahydrofuran. The mixture was cooled to -78 C in a dry ice-ethanol bath and then n-butyllithium (66 mL, 165 mmol) was added. A solution of di-tert-butyl azodicarboxylate (20.1 g, 87.4 mmol) in 80 mL of dry tetrahydrofuran was added dropwise under stirring at the same temperature. Upon completion of the addition, the dry ice-ethanol bath was removed and the mixture was warmed up to room temperature and stirred overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The reaction was quenched with 100 mL of water and the layers were separated. The aqueous layer was extracted with ethyl acetate (100 mLx2). The combined organic extracts were washed with saturated brine (150 mL¡Á1), dried over anhydrous sodium sulfate and filtered to remove the drying agent. The filtrate was purified by silica gel column chromatography to obtain the title compound N-(bicyclo[4.2.0]octa-1(6),2,4-trienyl-3-yl)-N’-(tert-butoxycarbonyl-hydrazino)-tert-butyl-carbonate 5c (4.07 g, 16.5%) as a yellow oil.
The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2236500; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary