Reaktion #61612

Reaktionsgleichung

2-iodo-3-nitro-benzoic acid methyl ester

1-chloro-4-ethynylbenzene

triethylamine

→

3-amino-2-(4-chloro-phenylethynyl)-benzoic acid methyl ester

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeArgon was bubbled through the resulting solution for 15 min
2. 2
   WaschenThe reaction mixture was then washed once with water
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe orange oil was purified by flash chromatography
6. 6
   Wascheneluting with 50 to 100% CHCl3/hexanes

Vorschrift

2-iodo-3-nitro-benzoic acid methyl ester (0.79 g, 2.84 mmol), 1-chloro-4-ethynylbenzene (0.41 g, 2.99 mmol), palladium tetrakis(triphenylphosphine) (0.16 g, 0.14 mmol), copper (I) iodide (0.03 g, 0.14 mmol), and triethylamine (1.44 g, 14.19 mmol) were dissolved in 15 mL toluene. Argon was bubbled through the resulting solution for 15 min. The reaction was stirred under argon at 80° C. for 2 h and 20 min. The reaction mixture was then washed once with water, dried (MgSO4), and concentrated in vacuo. The orange oil was purified by flash chromatography eluting with 50 to 100% CHCl3/hexanes to yield 3-amino-2-(4-chloro-phenylethynyl)-benzoic acid methyl ester, 0.76 g (94%) as a yellow oil. 1H NMR (300 MHz, d6-DMSO) δ 3.84 (s, 3H), 5.84 (br s, 2H), 6.97 (dd, J=8.1, 1.3 Hz, 1H), 7.05 (dd, J=7.5, 1.2 Hz, 1H), 7.17 (app t, J=7.5 Hz, 1H), 7.49 (d, J=8.7 Hz, 2H), 7.63 (d, J=8.7 Hz, 2H). MS (electrospray, MH+) 286.

Quelle