반응 #356648

반응 방정식

water

1,3,5-tribromobenzene

nBuLi

→

2-(3,5-Dibromophenyl)-1H-indene

용매

—

hexanes

ether

ether

반응 조건

후처리

1. 1
   workup.STIRRINGwhile vigorously stirring
2. 2
   workup.STIRRINGit was stirred at this temperature for 24 h
3. 3
   기타The organic layer was separated
4. 4
   추출the aqueous layer was extracted with 3×50 ml of dichloromethane
5. 5
   건조The combined organic layers were dried over Na2SO4
6. 6
   기타evaporated to dryness
7. 7
   workup.DISSOLUTIONThe residue was dissolved in 250 ml of toluene
8. 8
   workup.ADDITION0.75 g of p-TosOH was added
9. 9
   온도The resulting solution was refluxed for 1 hours
10. 10
    기타to remove the water
11. 11
    기타formed
12. 12
    기타Next, the mixture was evaporated to dryness
13. 13
    기타the product was isolated by flash-chromatography on Silica Gel 60 (d 50 mm, l 400 mm, eluent: hexanes)

실험 절차

To a solution of 12.6 g (40.0 mmol) of 1,3,5-tribromobenzene in 400 ml of ether, 160 ml (40.0 mmol) of 0.25 M nBuLi in hexanes was added for 1 h at −80° C. The mixture was stirred for 1.5 h at this temperature, and then a solution of 5.29 g (40.0 mmol) of indanone-2 in 200 ml of ether was added dropwise over 1 hour while vigorously stirring. The reaction mixture was allowed to warm to room temperature and it was stirred at this temperature for 24 h. Then, 100 ml of water was added. The organic layer was separated; the aqueous layer was extracted with 3×50 ml of dichloromethane. The combined organic layers were dried over Na2SO4 and then evaporated to dryness. The residue was dissolved in 250 ml of toluene, and 0.75 g of p-TosOH was added. The resulting solution was refluxed for 1 hours using a Dean-Stark trap to remove the water formed. Next, the mixture was evaporated to dryness, and the product was isolated by flash-chromatography on Silica Gel 60 (d 50 mm, l 400 mm, eluent: hexanes). Yield 8.54 g (61%) of white powder.

출처