反応 #2186184

反応方程式

compound ( b66 )

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

boron tribromide

water

→

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

収率 86.2%

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他The resulting reaction mixture
2. 2
   workup.WAITthe mixture was left at rest
3. 3
   その他to separate into an organic layer
4. 4
   抽出by extracting to the organic layer
5. 5
   洗浄The resulting organic layer was washed with a sodium chloride aqueous solution in three times
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他to obtain a residue
9. 9
   その他19.7 g of the residue was purified by recrystallization from a mixed solvent of heptane and toluene (heptane/toluene=2/1 by volume)

実験手順

22.0 g of the compound (b66) was dissolved in 200 mL of methylene chloride. 23.7 g of boron tribromide was added dropwise to the resulting solution in a temperature range of −27 to −20° C., and the temperature of the solution was gradually increased to room temperature, followed by stirring overnight. The resulting reaction mixture was poured slowly to 300 mL of iced water, and 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 with a sodium chloride aqueous solution in three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a residue. The residue was a yellowish solid. 19.7 g of the residue was purified by recrystallization from a mixed solvent of heptane and toluene (heptane/toluene=2/1 by volume) to obtain 18.0 g of 3-chloro-2-fluoro-4′-propylbiphenyl-4-ol (b67). The resulting compound (b67) was a white solid.

出典