Reaction #2348107

Reaction equation

Bromine

4-chloro-o-anisidine

→

4-chloro-5-bromo-2-aminoanisole

Yield 33.4%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherquenched with NaOH
2. 2
   WashThe organic layer was washed with brine
3. 3
   Dryingdried over MgSO4
4. 4
   Concentrationconcentrated
5. 5
   OtherPurification by flash chromatography over silica gel (elution with 10% ethyl acetate in hexanes)

Procedure

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