Reaction #1543

Reaction equation

2,6-diphenyl-4(3H)-pyrimidinone

N-bromosuccinimide

→

5-bromo-2,6-diphenyl-4(3H)-pyrimidinone

Yield 48.3%

Solvents

acetic acid

Conditions

Workup

1. 1
   workup.WAITthe mixture was left
2. 2
   workup.ADDITIONThe reaction was poured onto 100 g
3. 3
   Othercrushed ice and vacuum
4. 4
   Filtrationfiltered
5. 5
   Washwashing well with water
6. 6
   Otherair dried

Procedure

To a suspension of 13.37 g (56 mmol) of 2,6-diphenyl-4(3H)-pyrimidinone and 200 mL glacial acetic acid was added 15.1 g (84.8 mmol) of N-bromosuccinimide and the mixture was left to stir at room temperature for 60 h. The reaction was poured onto 100 g crushed ice and vacuum filtered, washing well with water, then air dried to yield 8.85 g (48%) 5-bromo-2,6-diphenyl-4(3H)-pyrimidinone, as a white solid. 1H-NMR (d6DMSO) δ 7.55(6H,m); 7.75(2H,m); 8.15(2H,m).

Source