反应详情

温度

-78 °C

To a cooled (−78° C.) solution of 4-[5-(3,4-dichlorophenyl)pentyl]-phenylamine (0.231 g, 0.75 mmol) in THF (2 mL), LHDMS (2.25 mL, 1 M in hexane, 2.25 mmol) was added dropwise. The reaction mixture was allowed to stir at −78° C. for 10 minutes. A solution of 2-fluoro-5-nitrobenzoic acid (0.139 g, 0.75 mmol) in THF (2 mL) was added dropwise, and this solution was stirred for 30 minutes at −78° C. The reaction mixture was allowed to gradually warm to room temperature and stir for 2 hours under N2 atmosphere. The reaction mixture was diluted with EtOAc, and acidified with 1N HCl (pH 3). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to yield a brown residue. Purification by flash chromatography (silica gel, 2% MeOH/CH2Cl2) then recrystallization with MeOH yielded 265 mg (0.56 mmol, 75%) of the desired product. mp 147-148° C.

1. additionwas added dropwise
2. stirringthis solution was stirred for 30 minutes at −78° C
3. temperatureto gradually warm to room temperature
4. stirringstir for 2 hours under N2 atmosphere
5. dry with materialThe organic layer was dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto yield a brown residue
9. customPurification by flash chromatography (silica gel, 2% MeOH/CH2Cl2)
10. customrecrystallization with MeOH