Extracurricular laboratory: Synthetic route of 19932-85-5

19932-85-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one, and cas is 19932-85-5, its synthesis route is as follows.

6-bromo-3H-1,3-benzoxazol-2-one (8A) (1.78g, 13 mmol) was dissolved in tetrahydrofuran (15 ml), and under N2 protection, a solution of 2M isopropyl magnesium chloride in tetrahydrofuran (7 mL, 14 mmol) were added at -10C. The temperature was raised to 0C, followed by reaction for 1 hour. A solution of n-butyllithium in tetrahydrofuran (21 ml, 52 mmol) was added at -25C, followed by reaction at -10C for 30 min. N,N-dimethylformamide (9.5 g, 130 mmol) was added at -10C, and the temperature was gradually raised to room temperature, followed by reaction for 0.5 hours. The reaction solution was poured into water (50 ml) containing 5 g citric acid, and was extracted by addition of ethyl acetate (50 ml). The aqueous phase was extracted with ethyl acetate (50 mL*1). The organic phases were combined. The organic phase was dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure, made into a slurry with 50% (v/v) ethyl acetate/petroleum ether, and purified by silica gel column chromatography (ethyl acetate/petroleum ether (v/v) = 0:1 to 1:4) to obtain the title compound 2-oxo-3H-1,3-benzoxazole-6-carbaldehyde (8B) as a white solid (1.60 g, yield 75.4%). 1H NMR (400 MHz, DMSO-d6) delta 12.16 (s, 1H), 9.92 (s, 1H), 7.78 (dd, 1H), 7.74 (d, 1H), 7.29 (d, 1H). LCMS m/z=164.1[M+1].

19932-85-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; WEI, Yonggang; QIU, Guanpeng; LEI, Bolin; LU, Yonghua; ZHENG, Suxin; EP3375781; (2018); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem