Reaktion #535536

Reaktionsgleichung

3-iodophthalic acid dimethyl ester

2,5-dimethoxyaniline

rac-BINAP

cesium carbonate

→

3-(2,5-Dimethoxyphenylamino)phthalic acid dimethyl ester

Ausbeute 68.0%

Lösungsmittel

CH2Cl2

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux under nitrogen for 24 hours
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Filtrationfiltered through Celite
4. 4
   Waschenthe filter was washed with additional CH2Cl2 (30 mL)
5. 5
   SonstigeThe filtrate was evaporated
6. 6
   Sonstigethe residue was chromatographed
7. 7
   Wascheneluting 0.73 g of the product at 80:20 hexanes-ethyl acetate

Vorschrift

A mixture of 3-iodophthalic acid dimethyl ester (1.0 g, 3.1 mmol), 2,5-dimethoxyaniline (0.48 g, 3.1 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), rac-BINAP (0.058 g, 0.093 mmol), and cesium carbonate (1.4 g, 4.3 mmol), in 6 mL toluene was heated to reflux under nitrogen for 24 hours. The reaction mixture was cooled, diluted with CH2Cl2 (10 mL), and filtered through Celite, and the filter was washed with additional CH2Cl2 (30 mL). The filtrate was evaporated, and the residue was chromatographed using a hexanes-ethyl acetate gradient, eluting 0.73 g of the product at 80:20 hexanes-ethyl acetate, in 68% yield: 1H NMR (CDCl3) δ 3.74 (s, 3H), 3.85 (s, 3H), 3.88 (s, 3H), 3.89 (s, 3H), 6.48 (dd, J=8.8 Hz, J=2.9 Hz, 1H), 6.83 (d, J=8.8 Hz, 1H), 6.87 (d, J=2.9 Hz, 1H), 7.19 (dd, J=7.7 Hz, J=0.9 Hz, 1H), 7.34 (t, J=7.9 Hz, 1H), 7.55 (dd, J=8.5 Hz, J=0.9 Hz, 1H), 7.95 (br, 1H).

Quelle