2-HYDROXYPHENYLBORONIC ACID THP-ETHER synthesis

4synthesis methods

Product Name:2-HYDROXYPHENYLBORONIC ACID THP-ETHER
CAS Number:502159-01-5
Molecular formula:C11H15BO4
Molecular Weight:222.05

57999-46-9 Synthesis

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Yield:502159-01-5 73.4%

Reaction Conditions:

Stage #1: 2-(tetrahydropyran-2-yloxy)phenyl bromidewith n-butyllithium in tetrahydrofuran;hexane at -78; for 0.5 h;Inert atmosphere;
Stage #2: Triisopropyl borate in tetrahydrofuran;hexane at -78;Inert atmosphere;

Steps:

2

Under a nitrogen atmosphere, 20.57g (80mmol, 1eq.) of compound 5 was dissolved in 200mL of ultra-dry tetrahydrofuran, the temperature of the system dropped to -78°C, and 48.0m, 2mol/L L n-butyllithium (96mmol, 1.2eq. .) in hexane solution, react at -78 for 30min, then slowly add 16.55g triisopropyl borate (88mmol, 1.1eq) dropwise, slowly return to room temperature, add 10.0mL water to quench, concentrate the reaction solution, ethyl acetate Ester extraction, washing with saturated brine, combining the organic phases, drying with anhydrous sodium sulfate, concentrating the filtrate, adding n-hexane to recrystallize and washing to obtain 13.04 g of white solid compound 6 with a yield of 73.4%.

References:

CN111943977,2020,A Location in patent:Paragraph 0129; 0143; 0145