Water → 4-methyl-2,6-diphenylphenol

A mixed solution of 1 mL of water and 4 mL of dimethoxyethane was added into a flask into which 2,6-dibromo-4-methylanisole (400 mg, 1.43 mmol), phenylboronic acid (535 mg, 4.39 mmol), palladium acetate (14 mg, 0.062 mmol), triphenylphosphine (60 mg, 0.23 mmol), and potassium phosphate (940 mg, 4.43 mmol) were already added, and then refluxed at normal temperature for 6 hours. After cooling to normal temperature, an ammonium chloride aqueous solution (5 mL) and 10 mL of diethylether were added thereto to separate an organic layer and extract residues using diethylether. The separated organic layer was dried with magnesium sulfate and volatile materials were removed to produce 420 mg of grey 4-methyl-2,6-diphenylanisole solid. The anisole thus produced was dissolved in 5 mL of methylene chloride without separate purification, 3 mL of boron tribromide (1 M methylene chloride solution) were dropped thereonto at −78° C., and the reaction was carried out while the temperature was slowly increased to normal temperature. After the reaction, a mixed solution of water (5 mL) and diethylether (10 mL) was added to separate an organic layer and extract an aqueous solution layer using diethylether (5 mL×3), and the separated organic layer was dried. Residues from which volatile components were removed at reduced pressure were purified using a silica gel chromatography tube in a mixed solvent of hexane and methylene chloride to produce 333 mg of white 4-methyl-2,6-diphenylphenol solid.

1. customwithout separate
2. custompurification, 3 mL of boron tribromide (1 M methylene chloride solution)
3. additionwere dropped
4. customat −78° C.
5. temperaturewas slowly increased to normal temperature
6. customAfter the reaction
7. customto separate an organic layer
8. extractionextract an aqueous solution layer
9. customthe separated organic layer was dried
10. customResidues from which volatile components were removed at reduced pressure
11. customwere purified

ORD record

ord-82dd4d522363414098bccdcacc270c78

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589042B2