Trimethyl borate → 4-Ethoxy-3-fluoro-2-formylphenylboronic acid

温度

-70 °C

Under a nitrogen atmosphere, n-BuLi (43.3 mL, 71.42 mmol) was slowly added dropwise, at −70° C. or lower, to a THF (200 mL) solution of compound (54) (19.8 g, 68.02 mmol). The reaction mixture was agitated at −70° C. or lower for 1 hour, and then trimethyl borate (10.6 g, 102.0 mmol) was slowly added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 200 mL of 2N hydrochloric acid aqueous solution, and extracted with 100 mL of toluene three times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was washed with heptane, and thus (4-ethoxy-3-fluoro-2-formylphenyl)boronic acid (55) (9.85 g, yield 68.3%) was obtained.

1. customwas returned to room temperature
2. customquenched with 200 mL of 2N hydrochloric acid aqueous solution
3. extractionextracted with 100 mL of toluene three times
4. washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
5. dry with materialdried over magnesium sulfate
6. distillationa solvent was distilled off by an evaporator
7. washThe residue was washed with heptane

ORDレコード

ord-8f159497c2f04ec197d2f92f54293010

出典データセット

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09193908B2