反応 #77698

反応方程式

tributylborate

4-iodotoluene

n-butyllithium

→

desired material

収率 85.2%

4-Methylphenylboronic acid

収率 85.2%

溶媒

diethyl ether

反応条件

後処理

1. 1
   温度was cooled to −60° C.
2. 2
   その他The cooling bath was removed
3. 3
   温度to heat up to room temperature
4. 4
   その他the organic phase separated off
5. 5
   抽出The aqueous phase was extracted with diethyl ether 2×125 mL)
6. 6
   抽出The combined organic phases were extracted with sodium hydroxide (1 N, 5×50 mL)

実験手順

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.

出典