Reaktion #2158221

Reaktionsgleichung

NaNO2

EtOAc

2,6-dibromo-4-tert-butylaniline

H2SO4

→

1,3-dibromo-5-tert-butylbenzene

Lösungsmittel

H2O

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers separated
2. 2
   WaschenThe organic layer was washed with 40 mL of brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification by flash silica gel chromatography (hexanes)

Vorschrift

To a stirring solution of 2,6-dibromo-4-tert-butylaniline in 115 mL of EtOH was added 11.5 mL of concentrated H2SO4. To the stirring solution at 90° C. was added 8.8 g of NaNO2 in several portions. After 37 h, EtOAc and 120 mL of H2O were added, and the layers separated. The organic layer was washed with 40 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (hexanes) provided 8.15 g of 1,3-dibromo-5-tert-butylbenzene as a yellow-brown oil with some impurity.

Quelle