Reacción #77698

Ecuación de reacción

tributylborate

4-iodotoluene

n-butyllithium

→

desired material

Rendimiento 85.2%

4-Methylphenylboronic acid

Rendimiento 85.2%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas cooled to −60° C.
2. 2
   OtroThe cooling bath was removed
3. 3
   Temperaturato heat up to room temperature
4. 4
   Otrothe organic phase separated off
5. 5
   ExtracciónThe aqueous phase was extracted with diethyl ether 2×125 mL)
6. 6
   ExtracciónThe combined organic phases were extracted with sodium hydroxide (1 N, 5×50 mL)

Procedimiento

To a solution of 4-iodotoluene (35 g, 160.5 mmol) in diethyl ether (400 mL) was added n-butyllithium (2 M in pentane, 88.3 mL, 176.6 mmol) at 0° C. After stirring at 0° C. for another 15 min the solution was cooled to −60° C. and tributylborate (60.6 mL, 224.7 mmol) was added. The cooling bath was removed and the reaction allowed to heat up to room temperature. The solution was acidified with hydrochloric acid (2 N, 280 mL) and the organic phase separated off. The aqueous phase was extracted with diethyl ether 2×125 mL). The combined organic phases were extracted with sodium hydroxide (1 N, 5×50 mL). The combined aqueous extracts were acidified to give 18.6 g of the desired material.

Fuente