反应详情

To a cooled solution (0 degrees Celcius) of acetoxy-(4-bromo-phenyl)-acetic acid (6.1 g, 22 mmol) in dichloromethane (30 mL) was added oxalyl chloride (4.2 g, 33 mmol) dropwise. After stirring for an additional 1 hour at room temperature, the reaction mixture was concentrated in vacuo and dried under vacuum. The acid chloride intermediate was dissolved in dichloromethane (20 mL) and then added over 1 hr to a solution of 4-trifluoromethylaniline (4.0 g, 25 mmol) and triethylamine (3.6 mL, 25 mmol) in dichloromethane (10 mL) at 0 degrees Celcius. The reaction was then allowed to warm to room temperature and stirred for 30 minutes. The reaction was diluted with dichloromethane and then washed twice with 1N HCl, twice with saturated sodium bicarbonate, and twice with brine. The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo to furnish a yellow solid. The solid was washed with ether to obtain a white solid (5.7 g, 61%).

1. concentrationthe reaction mixture was concentrated in vacuo
2. customdried under vacuum
3. dissolutionThe acid chloride intermediate was dissolved in dichloromethane (20 mL)
4. temperatureto warm to room temperature
5. stirringstirred for 30 minutes
6. washwashed twice with 1N HCl, twice with saturated sodium bicarbonate
7. dry with materialThe organic layer was then dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto furnish a yellow solid
11. washThe solid was washed with ether