Water → 3-(3-Cyanophenyl)benzyl alcohol

To a solution of 3-bromobenzonitrile (1.20 g, 6.58 mmol) in toluene (40 mL) was added a solution of tetrakistriphenylphosphinepalladium (0.38 g, 0.33 mmol), 2N aqueous sodium carbonate solution (21 mL) and [3-(hydroxymethyl)phenyl]boronic acid (1.00 g, 6.58 mmol) in EtOH (19 mL), and the mixture was heated under reflux for 10 hr under nitrogen atmosphere. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/9→1/1) to give the title compound as a yellow oil (1.28 g, 93%).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 10 hr under nitrogen atmosphere
3. extractionthe mixture was extracted with ethyl acetate
4. dry with materialThe organic layer was dried over sodium sulfate
5. concentrationconcentrated
6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/9→1/1)

ORD record

ord-e5e4c2741ffa45b0a2e4eee8aecdc351

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915267B2