Réaction #2186184

Équation de réaction

compound ( b66 )

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

boron tribromide

water

→

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

Rendement 86.2%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   AutreThe resulting reaction mixture
2. 2
   workup.WAITthe mixture was left at rest
3. 3
   Autreto separate into an organic layer
4. 4
   Extractionby extracting to the organic layer
5. 5
   LavageThe resulting organic layer was washed with a sodium chloride aqueous solution in three times
6. 6
   Séchagedried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   Autreto obtain a residue
9. 9
   Autre19.7 g of the residue was purified by recrystallization from a mixed solvent of heptane and toluene (heptane/toluene=2/1 by volume)

Mode opératoire

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.

Source