반응 #82570

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N-bromosuccinimide

4,5-difluoro-2-nitroaniline

N-bromosuccinimide

H2O

ethyl acetate

→

2-Bromo-3,4-difluoro-6-nitroaniline

용매

—

hexanes

DMF

DMF

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후처리

1. 1
   workup.STIRRINGthe reaction stirred another 12 h
2. 2
   추출the resulting cloudy suspension extracted with 3×20 mL methylene chloride
3. 3
   세척The combined organic phases were washed with 4×25 mL H2O and 25 mL saturated NaCl solution
4. 4
   건조dried (MgSO4)
5. 5
   여과filtered
6. 6
   기타the solvent rotary evaporated
7. 7
   기타to yield a yellow brown oil which
8. 8
   기타slowly crystallized
9. 9
   기타to yield 700 mg (96%)

실험 절차

2-Bromo-3,4-difluoro-6-nitroaniline was prepared using an adaptation of the method of Mitchell et al. (Mitchell, R. H. et al., J. Org. Chem. 44:4733 (1979)). To a solution of 4,5-difluoro-2-nitroaniline (500 mg, 2.87 mmol) in DMF (25 mL) under N2 was added all at once N-bromosuccinimide (511 mg, 2.87 mmol) in dry DMF (16 mL). The reaction was allowed to stir overnight. TLC (1:1 hexanes:ethyl acetate) showed still some starting material present. Additional N-bromosuccinimide (100 mg) was added and the reaction stirred another 12 h. The solution was then poured into 100 ml H2O and the resulting cloudy suspension extracted with 3×20 mL methylene chloride. The combined organic phases were washed with 4×25 mL H2O and 25 mL saturated NaCl solution and dried (MgSO4). The MgSO4 was vacuum filtered and the solvent rotary evaporated to yield a yellow brown oil which slowly crystallized to yield 700 mg (96%). 1H NMR (CDCl3) δ6.70 (br s, 2H, NH2), 7.99 (m, 1H, H-5).

출처