반응 #557554

반응 방정식

4-iodo-2-methyl-6-nitroaniline

2-bromo-2,2-difluoroacetic acid ethyl ester

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title compound

수율 65.3%

(4-Amino-3-methyl-5-nitro-phenyl)-difluoro-acetic acid ethyl ester

수율 65.3%

용매

DMSO

반응 조건

후처리

1. 1
   기타The mixture was purged with N2
2. 2
   온도After being cooled to the room temperature
3. 3
   workup.ADDITIONthe reaction mixture was poured into 20% aqueous NH4Cl solution (300 mL)
4. 4
   추출was extracted with EtOAc (3×100 mL)
5. 5
   추출The organic extract
6. 6
   세척was washed with brine (2×30 mL)
7. 7
   건조dried over Na2SO4
8. 8
   농축concentrated
9. 9
   기타The residue was purified by chromatography (40:1 hexanes/EtOAc)

실험 절차

To a solution of 4-iodo-2-methyl-6-nitroaniline (2.78 g, 10 mmol) and 2-bromo-2,2-difluoroacetic acid ethyl ester (2.03 g, 10 mmol) in anhydrous DMSO (20 mL) was added copper powder (1.28 g, 20 mmol). The mixture was purged with N2 and heated at 60° C. in a sealed vial for 14 h. After being cooled to the room temperature, the reaction mixture was poured into 20% aqueous NH4Cl solution (300 mL). The resulting mixture was basified to pH=8.5 with saturated aqueous Na2CO3 solution and was extracted with EtOAc (3×100 mL). The organic extract was washed with brine (2×30 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography (40:1 hexanes/EtOAc) to afford the title compound (1.79 g, 65%). 1H NMR (CDCl3) δ 1.36 (t, 3H), 2.30 (s, 3H), 4.36 (q, 2H), 6.41 (br s, 2H NH), 7.51 (s, 1H), 8.33 (s, 1H). ESI-MS m/z 275 (MH+), 255 (M-F)+, 297 (M+Na)+, 549 (2M+1)+ and 571 (2M+Na)+.

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