Reacción #2348107

Ecuación de reacción

Bromine

4-chloro-o-anisidine

→

4-chloro-5-bromo-2-aminoanisole

Rendimiento 33.4%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with NaOH
2. 2
   LavadoThe organic layer was washed with brine
3. 3
   Secadodried over MgSO4
4. 4
   Concentraciónconcentrated
5. 5
   OtroPurification by flash chromatography over silica gel (elution with 10% ethyl acetate in hexanes)

Procedimiento

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).

Fuente