Hydrochloric Acid → 3-Fluoro-5-(trifluoromethyl)benzeneboronic acid

Temperatur

-78 °C

In a second reaction vessel, 40 mL of tetrahydrofuran is cooled to -78° C., and 2.3 mL (0.021 mole) of trimethyl borate is added dropwise as the Grignard reagent of 3-fluoro-5-trifluoromethylphenyl bromide prepared above is transferred into the second reaction vessel using a cannula. The temperature of the reaction mixture is maintained below -60° C. during the additions. Upon completion of the additions, the reaction mixture is again cooled to -78° C., where it is stirred for about 45 minutes. After this time, the reaction mixture is allowed to warm to ambient temperature. The reaction mixture is then poured into about 200 mL of water and is made acidic with aqueous 5% hydrochloric acid. The mixture is extracted with four 100 mL portions of ethyl acetate. The combined extracts are dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 3.3 grams of 3-fluoro-5-trifluoromethylphenylboronic acid, mp 167°-168° C. The NMR spectrum is consistent with the proposed structure.

1. customprepared above
2. temperatureThe temperature of the reaction mixture is maintained below -60° C. during the additions
3. temperatureto warm to ambient temperature
4. extractionThe mixture is extracted with four 100 mL portions of ethyl acetate
5. dry with materialThe combined extracts are dried with magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate is concentrated under reduced pressure

ORD-Eintrag

ord-52a07fb681da4c5a990490bfc98bd888

Quelldatensatz

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05593998