Phenylboronic Acid → 3-Chloro-4-methyl-1,1'-biphenyl

To a suspension of tetrakis(triphenylphosphine)palladium (213 mg) in toluene (7 ml) was added 2-chloro-4-iodotoluene (2.33 g) at room temperature. The mixture was stirred at room temperature for 30 min, and a solution of phenylboronic acid (1.35 g) in ethanol (2 ml) and 2 M aqueous sodium carbonate solution (9.25 ml) were added to this mixture, which was followed by reflux under heating. After 3 hr, the reaction mixture was cooled and the organic layer was separated. The aqueous layer was extracted with hexane (4 ml). The organic layers were combined, washed with saturated aqueous sodium hydrogen carbonate solution (4 ml) and saturated brine (4 ml), and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated. To the residue (2.11 g) were added hexane (10 ml) and silica gel (4 g) and the mixture was stirred at room temperature for 1 hr. Silica gel was filtered off and the filtrate was concentrated to give 2-chloro-4-phenyltoluene as a pale-brown oil (1.86 g, 99.4%).

1. temperatureby reflux
2. temperatureunder heating
3. waitAfter 3 hr
4. temperaturethe reaction mixture was cooled
5. customthe organic layer was separated
6. extractionThe aqueous layer was extracted with hexane (4 ml)
7. washwashed with saturated aqueous sodium hydrogen carbonate solution (4 ml) and saturated brine (4 ml)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationAfter filtration
10. concentrationthe filtrate was concentrated
11. additionTo the residue (2.11 g) were added hexane (10 ml) and silica gel (4 g)
12. stirringthe mixture was stirred at room temperature for 1 hr
13. filtrationSilica gel was filtered off
14. concentrationthe filtrate was concentrated

ORD record

ord-2f83db0feb4644d79665dfbc2c8d6702

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06890934B2