반응 #160561

반응 방정식

2,3,4-trifluoronitrobenzene

2-fluoro-4-iodoaniline

LHMDS

→

crude product

2,3-Difluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline

용매

THF

THF

THF

반응 조건

후처리

1. 1
   기타The solution was transferred via cannula to a dropping funnel
2. 2
   workup.ADDITIONAfter completion of addition the mixture
3. 3
   추출followed by extraction
4. 4
   건조The organic layer was dried over sodium sulfate
5. 5
   기타the solvent was removed
6. 6
   기타the obtained dark oil was purified by flash chromatography (EtOAc/hexane 1:5, Rf=0.58)

실험 절차

To a solution of 2-fluoro-4-iodoaniline (11.40 g, 47 mmol) in 100 ml anhydrous THF at 0° C., 47 ml of a 1M solution of LHMDS in THF (47 mmol) was added dropwise. The color of the solution turned dark purple. The solution was transferred via cannula to a dropping funnel, and the solution (containing the amine free base) was added in small portions to a solution of 2,3,4-trifluoronitrobenzene (8.321 g, 47.0 mmol) in anhydrous THF (50 ml) at 0° C. After completion of addition the mixture was stirred under argon at room temperature for 15 hours. The volume of the solvent was reduced, followed by extraction using ethyl acetate and brine. The organic layer was dried over sodium sulfate, the solvent was removed, and the obtained dark oil was purified by flash chromatography (EtOAc/hexane 1:5, Rf=0.58) yielding the crude product, which became a brown solid upon drying in vacuo (yield: 6.23 g, 33.6%): m/z=393 [M−1]−.

출처