Reaktion #339995

Reaktionsgleichung

bromoarene

5-Brom0-2-nitro-phenylamine

prop-2-yn-1-ol

→

compound 72

Ausbeute 83.0%

3-(3-Amino-4-nitro-phenyl)-prop-2-yn-1-ol

Ausbeute 83.0%

Lösungsmittel

dichloromethane

ethyleneglycol dimethylether

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through a celite pad
2. 2
   Einengenconcentrated
3. 3
   SonstigePurification by flash chromatography (eluent 50 to 75% AcOEt in hexane)

Vorschrift

A suspension of bromoarene 2 (447 mg g; 2.06 mmol); tetrakis(triphenylphosphine) palladium(0) (145 mg, 0.12 mmol) and copper(I)iodide (143 mg, 0.75 mmol) in degassed ethyleneglycol dimethylether (2.5 mL) and triethylamine (1.5 mL), was stirred at room temperature under nitrogen in the dark for 10 min and then treated with neat prop-2-yn-1-ol (0.7 mL, 12 mmol) (or any other alkyne of choice, 5 eq.), and the mixture stirred under the same conditions for 48 h, diluted with dichloromethane (50 mL), filtered through a celite pad and concentrated. Purification by flash chromatography (eluent 50 to 75% AcOEt in hexane) afforded compound 72 (328 mg, 83% yield).

Quelle