Reaktion #54095

Reaktionsgleichung

4-Bromoaniline

magnesium sulfate

iodine

catechol

acetone

→

6-bromo-2,2,4-trimethyl-1,2-dihydroquinoline

Ausbeute 27.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction vessel was placed in a pre-equilibrated oil bath
2. 2
   Sonstigeset at 125° C.
3. 3
   Filtrationfiltered over a pad of diatomaceous earth
4. 4
   Einengenconcentrated in vacuo

Vorschrift

4-Bromoaniline (50 g, 0.290 mol), magnesium sulfate (250 g, 2 mol), iodine (2.5 g, 0.01 mol) and catechol (2.24 g, 0.020 mol) were combined in acetone (750 mL) in a sealed-tube reaction flask. The reaction vessel was placed in a pre-equilibrated oil bath set at 125° C. and stirred overnight. The reaction mixture was then cooled to room temperature, filtered over a pad of diatomaceous earth, and concentrated in vacuo. Chromatography on silica gel provided 6-bromo-2,2,4-trimethyl-1,2-dihydroquinoline as tan colored crystals (21 g, 27% yield).

Quelle