Water → 3-(Propan-2-yl)[1,1'-biphenyl]-2-ol

In a flask charged with 2-bromo-6-isopropylanisole (1.98 g, 8.64 mmol), phenylboronic acid (2.10 g, 17.28 mmol), palladium acetate (96 mg, 0.43 mmol), triphenylphosphine (0.225 g, 0.86 mmol) and potassium phosphate (11 g, 51.84 mmol), mixture of water (8 mL) and dimethoxyethane (32 mL) was added, and the resultant mixture was heated under reflux for 12 hours. After cooling to ambient temperature, aqueous ammonium chloride (15 mL) and diethyl ether (30 mL) were charged thereto. The organic layer was isolated, and the residue was extracted with diethyl ether. Combined organic layer was dried over magnesium sulfate, and evaporated to remove the volatiles to obtain 2-isopropyl-6-phenylanisole as grey solid (2 g). The anisole obtained (without further purification) was dissolved in methylene chloride (15 mL), and 12 mL of boron tribromide solution (1 M in methylene chloride) was added dropwise thereto at −78° C. Reaction was carried out for 12 hours while slowly raising the temperature to ambient temperature. When the reaction was completed, mixture of water (15 mL) and diethyl ether (30 mL) was added thereto. After isolating the organic layer, the aqueous layer was extracted with diethyl ether (15 mL×3). The combined organic layer was dried, and evaporated under reduced pressure to remove the volatiles. The residue was purified via silica gel column by using mixed solvent of hexane and methylene chloride to obtain 2-isopropyl-6-phenylphenol (1.72 g) as white solid.

1. custom(without further purification)
2. dissolutionwas dissolved in methylene chloride (15 mL)
3. addition12 mL of boron tribromide solution (1 M in methylene chloride) was added dropwise
4. customat −78° C
5. customReaction
6. additionwas added
7. customAfter isolating the organic layer
8. extractionthe aqueous layer was extracted with diethyl ether (15 mL×3)
9. customThe combined organic layer was dried
10. customevaporated under reduced pressure
11. customto remove the volatiles
12. customThe residue was purified via silica gel column
13. additionby using mixed solvent of hexane and methylene chloride

ORD record

ord-51630a6fee8145e1aa8df50155921c15

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067511B2