反应详情

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 thereto were added a solution of phenylboronic acid (1.35 g) in EtOH (2 ml) and 2M aqueous sodium carbonate solution (9.25 ml), and the mixture was refluxed 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 hydrogencarbonate solution (4 ml) and saturated brine (4 ml), and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated, and hexane (10 ml) and silica gel (4 g) were added to the residue (2.11 g). 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. temperaturethe mixture was refluxed
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 hydrogencarbonate 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. additionhexane (10 ml) and silica gel (4 g) were added to the residue (2.11 g)
12. stirringThe mixture was stirred at room temperature for 1 hr
13. filtrationSilica gel was filtered off
14. concentrationthe filtrate was concentrated