Triisopropyl borate → [4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid

Temperatur

-65 °C

A solution of methyllithium (8% w/w in diethoxymethane) (65 ml) was added to a suspension of 2-(4-bromophenyl)-1,3,4-oxadiazole (40 g) in tetrahydrofuran (THF) (415 ml) at −65° C. After an hour a solution of n-butyllithium (2.5M in hexanes) (78 ml) was then added at −65° C. After an hour, triisopropylborate (90 ml)) was then added maintaining the reaction mixture at −65° C. The reaction mixture was held at −65° C. for an hour and then warmed to −20° C. and drowned out into a mixture of acetic acid (28 ml) in water (222 ml). The resultant solid was isolated, washed with THF and water, and dried to yield the title compound (28.96 g@ 95.1% w/w, 82%); 400 MHz NMR Spectrum: (DMSOd6) 8.00 (s, 4H), 8.31 (s, 2H), 9.35 (s, 1H); Mass Spectrum MH+ 191.0628 (calc. using 11-B) Found 191.0633.

1. waitAfter an hour
2. waitThe reaction mixture was held at −65° C. for an hour
3. temperaturewarmed to −20° C.
4. customThe resultant solid was isolated
5. washwashed with THF and water
6. customdried

ORD-Eintrag

ord-9cfc45d53b9f4b5e9370cef76535023a

Quelldatensatz

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07626020B2