4-METHOXY-3-METHYLPHENYLBORONIC ACID synthesis
- Product Name:4-METHOXY-3-METHYLPHENYLBORONIC ACID
- CAS Number:175883-62-2
- Molecular formula:C8H11BO3
- Molecular Weight:165.98
5419-55-6
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175883-62-2
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Yield:-
Reaction Conditions:
Stage #1:2-methyl-4-bromoanisole with n-butyllithium in tetrahydrofuran;hexane at -78; for 1 h;
Stage #2:Triisopropyl borate in tetrahydrofuran;hexane at -78 - 25;
Steps:
4.2. General procedure for the preparation of compounds 2a-e
General procedure: To a solution of compound 1a-e (10.0 mmol,1.0 eq) in anhydrousTHF (20 mL) was slowly added n-BuLi (6 mL of 2.5 M solution inhexane, 15.0 mmol, 1.5 eq) at 78 °C. The mixture was stirred for1 h and triisopropyl borate (50.0 mmol, 5.0 eq) was added by syringe.The solutionwas stirred for another 1 h and allowed towarmto 25 C overnight. The reactionwas cooled to 0 C, followed by thesequential addition ofwater (5 mL) and 2N HCl (5 mL). After 10 min,an additional 35 mL of 2N HCl was added and the mixture wasfurther stirred for 30 min. The mixture was extracted with ethylacetate (20 mL * 3) and the combined organic layers wereconcentrated to a thick oil under reduced pressure. Crystallizationwith cold hexane yielded a white solid.
References:
Sang, Yali;Han;Pannecouque, Christophe;De Clercq, Erik;Zhuang, Chunlin;Chen [European Journal of Medicinal Chemistry,2019,vol. 182,art. no. 111603]
14804-31-0
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175883-62-2
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175883-62-2
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