Water → HCID 57793288, compound

HRID 2099002Notes

Reaction equation

HRID 2099002 reaction equation
[Cl:1][C:2]1[C:3]([F:19])=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([F:19])=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 577930683-Chloro-2-fluoro-4-methoxy-4′-propyl-1,1′-biphenyl

Product 1

HCID 57793288HCID 57793288, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. customThe resulting reaction mixture
  2. waitthe mixture was left at rest
  3. customto separate into an organic layer
  4. extractionby extracting to the organic layer
  5. washThe resulting organic layer was washed with a sodium chloride aqueous solution in three times
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain a residue
  9. custom19.7 g of the residue was purified by recrystallization from a mixed solvent of heptane and toluene (heptane/toluene=2/1 by volume)

Sources & evidence

ORD record
ord-7d7c046e958449359da2eea064547cb2
Source dataset
uspto-grants-2009_08
Patent number
US07569258B2

Reaction notes

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