Reaktion #359849

Reaktionsgleichung

methyl 4-chloro-2-iodobenzoate

4-bromo-2-nitroaniline

K2CO3

→

desired product

Ausbeute 89.0%

methyl 2-[(4-bromo-2-nitrophenyl)amino]-4-chlorobenzoate

Ausbeute 89.0%

Lösungsmittel

chlorobenzene

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 2 days
3. 3
   Filtrationfiltered through diatomaceous earth (Celite®)
4. 4
   WaschenThe solution was washed with water and brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under vacuum
8. 8
   SonstigeThe residue was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate

Vorschrift

A mixture of methyl 4-chloro-2-iodobenzoate (5.93 g, 20 mmol), 4-bromo-2-nitroaniline (4.34 g, 20 mmol), copper (1.26 g, 20 mmol), and K2CO3 (2.76 g, 20 mmol) in chlorobenzene (300 mL) was heated to reflux for 2 days, cooled to room temperature, diluted with ethyl acetate, and filtered through diatomaceous earth (Celite®). The solution was washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate to provide 6.86 g (89%) of the desired product. MS (DCI) m/e 386 (M+H)+, 403 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 10.83 (s, 1H), 8.28 (d, J=2.4 Hz, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.82 (dd, J=9.1, 2.4 Hz, 1H), 7.63 (d, J=9.1 Hz, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.17 (dd, J=8.5, 2 Hz, 1H), 3.87 (s, 3H).

Quelle