反応 #69895

反応方程式

Carbon dioxide

Butyllithium

diisopropylamine

4-bromopyridine hydrochloride

→

4-bromonicotinic acid

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting solution was stirred for 2 hours
2. 2
   workup.STIRRINGThe resulting solution was stirred overnight at room temperature
3. 3
   その他The reaction was then quenched with water (100 mL)
4. 4
   抽出The resulting solution was extracted with EtOAc (3×200 mL)

実験手順

Butyllithium (82.0 mL, 205.6 mmol, 2.0 eq.) was added dropwise to a solution of diisopropylamine (20.8 g, 205.6 mmol, 2.0 eq.) in THF (100 mL) at −78° C., under nitrogen. The resulting solution was stirred for 1 hour at approximately −60 to −50° C. The resulting solution was added dropwise to a solution of 4-bromopyridine hydrochloride (20.0 g, 102.9 mmol, 1.0 eq.) in THF (100 mL) at −78° C. The resulting solution was stirred for 2 hours. Carbon dioxide gas was introduced into the reaction vessel for 30 minutes. The resulting solution was stirred overnight at room temperature. The reaction was then quenched with water (100 mL). The resulting solution was extracted with EtOAc (3×200 mL) and the aqueous layers were combined. The pH of the solution was adjusted to 3-4 with 1N HCl to yield 4-bromonicotinic acid (16.8 g) as a white solid. ES m/z: [M+H]+ 202.

出典