Reaction #1106675

Reaction equation

3-bromo-5-tert-butylbenzaldehyde

malonic acid

ammonium acetate

→

product

Yield 51.6%

3-amino-3-(3-bromo-5-tert-butylphenyl)propionic acid

Yield 51.6%

Solvents

isopropanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux under nitrogen for 3 h
3. 3
   Otherto afford a thick colorless solid
4. 4
   FiltrationThe solid was filtered hot
5. 5
   Washwashed with hot isopropanol (2×25 mL)
6. 6
   Otherdried in vacuo

Procedure

A suspension of 3-bromo-5-tert-butylbenzaldehyde (4.17 g, 17.30 mmol), malonic acid (2.15 g, 20.72 mmol) and ammonium acetate (2.66 g, 34.59 mmol) in isopropanol (35 mL) was heated at reflux under nitrogen for 3 h to afford a thick colorless solid. The solid was filtered hot, washed with hot isopropanol (2×25 mL) and dried in vacuo to give the desired racemic product as a colorless solid (2.68 g).

Source