Water → 4-(2,6-Dimethylphenyl)benzyl alcohol

(4-Bromophenyl)methanol (5.00 g, 32 mmol), (2,6-dimethylphenyl)boronic acid (5.77 g, 39 mmol) and sodium carbonate (10.2 g, 96 mmol) were dissolved in toluene-methanol-water (5:1:1, 210 mL) and, after argon substitution, tetrakistriphenylphosphinepalladium (1.85 g, 1.6 mmol) was added. The reaction mixture was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (4.44 g, yield 65%) as a white powder.

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux overnight under an argon atmosphere
3. temperatureThe reaction mixture was cooled
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with water
6. customdried
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:3)

ORD record

ord-f0e51cde3e484437aca25064bbd1e0fb

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960369B2