Reaction #710579

Reaction equation

2-Bromo-4,5-dimethoxylbenzeneethanamine

phthaloyl dichloride

Hünig's base

→

crude product

2-Bromo-4,5-dimethoxyl-(2-phthalimidoethyl)benzene

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherAcetonitrile was then removed
2. 2
   Washwashed with basic water (pH=11)
3. 3
   WashThe aqueous wash
4. 4
   Extractionwas extracted with dichloromethane 3×15 mL
5. 5
   Dryingdried over sodium sulfate
6. 6
   OtherSolvent was removed

Procedure

2-Bromo-4,5-dimethoxylbenzeneethanamine (3.5 g 13.2 mmol) was dissolved and stirred in 50 mL dry acetonitrile. 2.14 mL (1.1 equiv) phthaloyl dichloride and 7 mL (3 equiv) Hünig's base were added. The mixture was stirred at room temperature overnight. Acetonitrile was then removed, and the remaining product was taken up in dichloromethane and washed with basic water (pH=11). The aqueous wash was extracted with dichloromethane 3×15 mL. The organic fractions were combined and dried over sodium sulfate. Solvent was removed to give the crude product, which was then purified by column chromatography. Calculated yield: 1.8 g (34%).

Source