Triisopropyl borate → {2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}boronic acid

Temperature

-78 °C

To a solution of 1-bromo-2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]benzene (D100) (930 mg, 3.83 mmol) in Tetrahydrofuran (THF) (10 mL) was added BuLi (1.989 mL, 4.97 mmol) dropwise at −78° C. under nitrogen. The reaction mixture was stirred at −78° C. for 2 hours. Tris(1-methylethyl) borate (1.319 mL, 5.74 mmol) was added to the reaction mixture by syringe at −78° C. Then the reaction was stirred at −78° C. for 30 min, and then warmed to room temperature slowly. Then the reaction was quenched with water. The mixture was extracted with EA (15 mL×3). The combined organic layers was dried over anhydrous sodium sulphate. After filtration and concentration, the crude {2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}boronic acid (D101) (741 mg) was used directly in the next step. MS (ES): C10H13BO4 requires 208.1. found 209.0 (M+H+)

1. stirringThen the reaction was stirred at −78° C. for 30 min
2. temperaturewarmed to room temperature slowly
3. customThen the reaction was quenched with water
4. extractionThe mixture was extracted with EA (15 mL×3)
5. dry with materialThe combined organic layers was dried over anhydrous sodium sulphate
6. filtrationAfter filtration and concentration

ORD record

ord-7c6bb231cefb4316a39223c4fab26790

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2