Potassium Hydroxide → 3-Fluoro-4-(methylthio)phenylboronic acid

온도

-40 °C

A solution of 4-bromo-2-fluorothioanisole (0.5 g, 22.6 mmol) in dry THF (20 mL) was chilled to −78° C. under a nitrogen atmosphere. The reaction mixture was treated with 1.6 M n-butyllithium in hexanes (1.7 mL, 27.1 mmol), and the mixture was warmed to −40° C. where it was maintained for 0.5 hours. The reaction mixture was then chilled to −78° C. and three equivalents of triisopropyl borate (1.56 mL, 67.8 mmol) were added. The reaction mixture was allowed to warm to room temperature and stirred for 1.5 hours. At this point, 10% aqueous KOH (200 mL, 360 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was then poured into an ice/concentrated HCl mixture with stirring to yield a white precipitate. This solid was dried in a vacuum oven (65° C., 29 in Hg) overnight to provide the title compound (yield: 0.22 g; 52.4%). 1H NMR (300 MHz, DMSO-d6) δ 2.48 (s, 3H), 7.31 (t, J=9 Hz, 1H), 7.49 (dd, J=12 Hz, 1.5 Hz, 1H) 7.54 (dd, J=9 Hz, 1.5 Hz, 1H).

1. temperaturewas maintained for 0.5 hours
2. temperatureThe reaction mixture was then chilled to −78° C.
3. temperatureto warm to room temperature
4. stirringthe mixture was stirred overnight at room temperature
5. stirringwith stirring
6. customto yield a white precipitate
7. customThis solid was dried in a vacuum oven (65° C., 29 in Hg) overnight

ORD 기록

ord-8bc461da6d574f799637c020184f5360

출처 데이터셋

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06307047B1