Hydrochloric Acid → 2-(Methylthio)benzeneboronic acid

Temperature

0 °C

A solution of 1-methylthio-2-bromobenzene (5 g) in dry ether (30 ml) was stirred at 0° C. and 1.63M n-butyllithium in hexane solution (16.6 ml) was added dropwise over a period of 15 minutes. The reaction mixture was stirred at 0° C. for 1.5 hours and then transferred to a cold (-78° C.) solution of triisopropyl borate (7.4 ml) in tetrahydrofuran (40 ml) over 40 minutes. After stirring for 1 hour at -78° C., the reaction mixture was allowed to warm to room temperature overnight. The suspension was poured into dilute 2M hydrochloric acid (40 ml) and the layers were separated. The aqueous phase was extracted with ether (2×80 ml) and the combined organic phases were washed with brine, dried with magnesium sulfate, evaporated and washed with petroleum ether (2×20 ml) to afford 2-methylthiophenyldihydroxyborane.

1. stirringAfter stirring for 1 hour at -78° C.
2. temperatureto warm to room temperature overnight
3. additionThe suspension was poured
4. customthe layers were separated
5. extractionThe aqueous phase was extracted with ether (2×80 ml)
6. washthe combined organic phases were washed with brine
7. dry with materialdried with magnesium sulfate
8. customevaporated
9. washwashed with petroleum ether (2×20 ml)

ORD record

ord-4fdc4de24c1844d5b47b1b78c2c6552a

Source dataset

uspto-grants-1998_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05824691