Trimethyl borate → 5-Sec-butyl-1-methoxy-benzene boronic acid

Temperature

-78 °C

2-Bromo-4-sec-butyl-1-methoxy-benzene (1.15 g) is dissolved in tetrahydrofuran (17 ml) and the mixture is cooled to −78° C., and thereto is added dropwise 1.6M n-butyllithium in hexanes, and the mixture is stirred at −78° C. for 15 minutes. To the reaction solution is added trimethyl borate (1.47 g), and the reaction mixture is stirred at −78° C. for 30 minutes, and thereto are added a saturated aqueous ammonium chloride solution and ethyl acetate. The mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give crude 5-sec-butyl-1-methoxy-benzene boronic acid (950 mg). NMR (CDCl3): 0.81 (3H, t), 1.22 (3H, d), 1.58 (2H, m), 2.58 (1H, m), 3.90 (3H, s), 6.25 (2H, s), 6.85 (2H, d), 7.25 (1H, d), 7.65 (1H, s).

1. stirringthe reaction mixture is stirred at −78° C. for 30 minutes
2. customThe mixture is separated
3. washthe organic layer is washed with a saturated brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-41d7710d29104a60b03e11c7c459f28a

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906517B2