반응 #2186185

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compound ( b67 )

3-chloro-2-fluoro-4′-propylbiphenyl-4-ol

potassium carbonate

water

toluene

→

3-chloro-2-fluoro-4-(trans-4-pentyl-cyclohexylmethoxy)-4′-propylbiphenyl

수율 89.5%

용매

N,N,-dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwere added to the reaction mixture
3. 3
   workup.ADDITIONby mixing
4. 4
   workup.WAITThereafter, the mixture was left at rest
5. 5
   기타to separate into an organic layer
6. 6
   추출by extracting to the organic layer
7. 7
   세척The resulting organic layer was washed sequentially with water
8. 8
   농축a 2N sodium hydroxide aqueous solution, a saturated sodium chloride aqueous solution and water, and then concentrated under reduced pressure
9. 9
   기타to obtain a residue
10. 10
    기타7.7 g of the residue was purified by a preparative column chromatography
11. 11
    기타further purified
12. 12
    기타recrystallization from a mixed solvent of heptane and Solmix A-11 (heptane/Solmix A-11=2/1 by volume)

실험 절차

4.0 g of the compound (b67) obtained in the second step was dissolved in 20 mL of N,N,-dimethylformamide. After suspending 2.5 g of potassium carbonate in the solution, 5.6 g of the compound (b68) was added thereto, followed by stirring for 6 hours at 70° C. After completing the reaction, water and toluene were added to the reaction mixture, followed by mixing. Thereafter, the mixture was left at rest to separate into an organic layer and an aqueous layer, followed by extracting to the organic layer. The resulting organic layer was washed sequentially with water, a 2N sodium hydroxide aqueous solution, a saturated sodium chloride aqueous solution and water, and then concentrated under reduced pressure to obtain a residue. 7.7 g of the residue was purified by a preparative column chromatography using a mixed solvent of heptane and toluene (heptane/toluene=3/1 by volume) as a developing solvent and silica gel as a mediator, and further purified by repeating recrystallization from a mixed solvent of heptane and Solmix A-11 (heptane/Solmix A-11=2/1 by volume) to obtain 3-chloro-2-fluoro-4-(trans-4-pentyl-cyclohexylmethoxy)-4′-propylbiphenyl (C264) as colorless crystals. The yield was 89.5% based on the compound (b67).

출처