반응 #85599

반응 방정식

2,2,6,6-Tetramethylpiperidine

N,N′,N″,N″-pentamethyldiethylene triamine

compound 1

4-methylcatechol

n-BuLi

THF

1,1,2-trichloro-1,2,2-trifluoroethane

→

title compound

수율 73.8%

4-chloro-5-fluoro-1H-indole-3-carboxylic acid

수율 73.8%

용매

Water

—

hexanes

반응 조건

후처리

1. 1
   온도was warmed to 25° C
2. 2
   세척The organic phase was washed with brine
3. 3
   건조dried with sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by SiO2 column chromatography (PE)

실험 절차

2,2,6,6-Tetramethylpiperidine (1.06 g, 7.5 mmol), N,N′,N″,N″-pentamethyldiethylene triamine (3.46 g, 20 mmol) and compound 1 (1.45 g, 5.0 mmol) were added consecutively to a solution of n-BuLi (2.5 M in hexanes, 8 mL, 20 mmol) in THF (20 mL) and hexanes (6 mL) at −78° C. After stirring for 4 h at −78° C., the mixture was treated with 1,1,2-trichloro-1,2,2-trifluoroethane (1.18 g, 6.0 mmol) before it was warmed to 25° C. Water was added to the mixture. The organic phase was washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by SiO2 column chromatography (PE) to provide title compound (1.2 g, 73.8%) as a colorless liquid.

출처