반응 #320309

반응 방정식

hydrogen chloride

aluminium trichloride

4-fluorobenzoyl chloride

thiophene

→

product

수율 71.6%

2-(4-Fluorobenzyl)thiophene

수율 71.6%

용매

chlorobenzene

chlorobenzene

반응 조건

후처리

1. 1
   기타absorbed in sodium hydroxide solution
2. 2
   기타the remaining hydrogen chloride was removed
3. 3
   workup.ADDITIONThe resulting solution was added dropwise to a suspension of 7.2 g of sodium borohydride in 47.2 g of digylme
4. 4
   workup.STIRRINGwhile stirring at 70° C. over the course of 45 minutes
5. 5
   workup.STIRRINGThe reaction mixture was then stirred for 90 minutes
6. 6
   온도cooled to room temperature
7. 7
   workup.ADDITIONdischarged into a mixture of 250 g of ice, 44.6 g of concentrated aqueous hydrochloric acid and 500 g of water
8. 8
   기타The organic phase which formed
9. 9
   기타thereby was separated off
10. 10
    추출the aqueous phase was extracted
11. 11
    workup.STIRRINGby shaking with chlorobenzene
12. 12
    workup.DISTILLATIONthe combined organic phases were distilled

실험 절차

33.8 g of aluminium trichloride were suspended in 217 g of chlorobenzene, and a solution of 40.3 g of 4-fluorobenzoyl chloride in 37.4 g of chlorobenzene was added dropwise to this at 0° C. over the course of 15 minutes. The mixture was then stirred for 1 hour and then, at 0° C., 21.8 g of thiophene were added dropwise over the course of 20 minutes. The resulting hydrogen chloride was drawn off and absorbed in sodium hydroxide solution. The mixture was subsequently heated to 80° C. and the remaining hydrogen chloride was removed. The resulting solution was added dropwise to a suspension of 7.2 g of sodium borohydride in 47.2 g of digylme while stirring at 70° C. over the course of 45 minutes. The reaction mixture was then stirred for 90 minutes and then cooled to room temperature and discharged into a mixture of 250 g of ice, 44.6 g of concentrated aqueous hydrochloric acid and 500 g of water. The organic phase which formed thereby was separated off, the aqueous phase was extracted by shaking with chlorobenzene, and the combined organic phases were distilled. 35.0 g of product with a boiling point of 83° C./1.0 mbar and a purity of 99.7% (GC) were obtained. This corresponds to 73.9% of theory. The product contained less than 0.1% by weight of defluorinated compounds (GC).

출처