With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,as a common compound, the synthetic route is as follows.
Intermediate 4. 2- oxo-2,3-dihydro-1 ,3-benzoxazole-6-carbaldehyde To a suspension of 6-bromobenzo[d]oxazol-2(3H)-one (6.12g, 28.6mmol) in THF (60ml_) was added, at -78 C and under argon atmosphere, methylmagnesium bromide (10.6ml_ of a 3M solution in diethyl ether, 31 .8mmol) and the reaction mixture was stirred at this temperature fro 30 min. The, an additional amount of THF (240 mL) was added at a rate that the internal temperature was below -50 C. Then, tert-butyllithium (60.6ml_ of a 1.7 M solution in pentane, 103mmol) was slowly added and stirred for 45 min at -78 C. To the yellow suspension DMF (13.4ml_, 181 mmol) was then added, and the reaction mixtures was allowed to warm up to room temperature and stirring wasa continued for 3 additional hours. Water (300ml_) was then added to the crude mixture and the organic solvent was removed under reduced pressure. To the remaining aqueous phase, ethyl acetate (500ml_) and 1 N HCI (150ml_) were added and the the mixture was vigorously stirred and the organic phase was separated. The aqueous phase was further extracted with ethyl acetate (3 x 100 mL) and the combined organic extracts were washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to yield the title compound (4.75g, 96%, 94% purity by UPLC). The compound was used as this without further purification. LRMS (m/z): 162 (M-1 )-
The synthetic route of 19932-85-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; ALMIRALL, S.A.; PUIG DURAN, Carlos; AIGUADE BOSCH, Jose; GUAL ROIG, Silvia; PRAT QUINONES, Maria; (149 pag.)WO2016/46390; (2016); A1;,
Benzoxazole – Wikipedia
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