4-Iodotoluene → Tolylboronic acid

Temperature

0 °C

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.

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

ORD record

ord-74803c53f6274e458b772a5e05af20cd

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06706749B2