With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1211539-82-0, name is 2,2-Difluorobenzo[d][1,3]dioxol-5-ol, molecular formula is C7H4F2O3, molecular weight is 174.1, as common compound, the synthetic route is as follows.Safety of 2,2-Difluorobenzo[d][1,3]dioxol-5-ol
To a solution of Example 194A (3.0 g, 17.23 mmol) in N,N-dimethylformamide (30 mL) at ambient temperature was added potassium carbonate (4.76 g, 34.5 mmol) and teri-butyl bromoacetate (2.91 mL, 19.82 mmol). This mixture was warmed to 65 C and was allowed to stir for 1.5 hours. The mixture was allowed to cool to ambient temperature and was then partitioned between ethyl acetate (50 mL) and 0 (50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3 x 15 mL). The combined organic fractions were dried over anhydrous Na2SO/t, filtered, and concentrated under reduced pressure to give 5.5 g of teri-butyl 2-((2,2-difluorobenzo[(f] [l ,3]dioxol-5-yl)oxy)acetate, which was used without further purification. To a mixture of teri-butyl 2-((2,2-difluorobenzo[i ] [l ,3]dioxol-5- yl)oxy)acetate (5.0 g, 17.35 mmol) in methanol (60 mL) and water (20.00 mL) was added NaOH (17.35 mL, 87 mmol, 5 M aqueous solution). This mixture was allowed to stir at ambient temperature for 2 hours, and then it was concentrated under reduced pressure. The residue was dissolved in water, and the pH was adjusted to ~1 with 1 N HC1. The resulting solid was collected by filtration to give the title compound (3.28 g, 14.13 mmol, 81% yield) as a white solid. JH NMR (400 MHz, DMSO-<) delta ppm 13.10 (s, 1H), 7.30 (d, / = 8.9 Hz, 1H), 7.13 (d, / = 2.6 Hz, 1H), 6.73 (dd, / = 8.9, 2.6 Hz, 1H), 4.69 (s, 2H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211539-82-0, 2,2-Difluorobenzo[d][1,3]dioxol-5-ol, and friends who are interested can also refer to it.
Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
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