Réaction #2348107

Équation de réaction

Bromine

4-chloro-o-anisidine

→

4-chloro-5-bromo-2-aminoanisole

Rendement 33.4%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrequenched with NaOH
2. 2
   LavageThe organic layer was washed with brine
3. 3
   Séchagedried over MgSO4
4. 4
   Concentrationconcentrated
5. 5
   AutrePurification by flash chromatography over silica gel (elution with 10% ethyl acetate in hexanes)

Mode opératoire

Bromine (26.4 g) was added to a solution of 4-chloro-o-anisidine (23.55 g) in dichloromethane (400 mL) at room temperature. The resulting mixture was stirred for 10 hours and quenched with NaOH. The organic layer was washed with brine, dried over MgSO4, and concentrated. Purification by flash chromatography over silica gel (elution with 10% ethyl acetate in hexanes) gave 11.8 g (33%) of the desired 4-chloro-5-bromo-2-aminoanisole. 1H NMR (300 MHz, CDC13) d 6.94 (s, 1 H), 6.78 (s, 1 H), 3.83 (s, 3 H).

Source