Reaction #710578

Reaction equation

Bromine

2-(3,4-dimethoxyphenyl)ethylamine

→

2-Bromo-4,5-dimethoxylbenzeneethanamine

Yield 79.2%

Solvents

acetic acid

acetic acid

Conditions

Workup

1. 1
   Other2-bromo-4,5-dimethoxylbenzeneethanamine precipitated out after 15 minutes
2. 2
   Filtrationfiltered
3. 3
   Washwashed with dichloromethane 10 mL×3 and petroleum ether 10 mL×3
4. 4
   ExtractionExtraction with dichloromethane
5. 5
   Otherfollowed by evaporation of the solvent

Procedure

Bromine (1.1 mL, 22 mmol) in acetic acid (10 mL) was slowly added into a vigorously stirred solution of 2-(3,4-dimethoxyphenyl)ethylamine (3.4 mL, 20 mmol) in 50 mL acetic acid. 2-bromo-4,5-dimethoxylbenzeneethanamine precipitated out after 15 minutes. The mixture was stirred for another two hours, filtered, and washed with dichloromethane 10 mL×3 and petroleum ether 10 mL×3. The resulting solid was taken up in water and the pH was brought to 10 with aqueous KOH solution. Extraction with dichloromethane followed by evaporation of the solvent yielded 4.12 g (78%) 2-Bromo-4,5-dimethoxylbenzeneethanamine. The crude product was dried under dynamic vacuum overnight and used without further purification.

Source