N-bromobutanimide → 5-bromo-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone

HRID 2400099Notes

Reaction equation

HRID 2400099 reaction equation
[C:1]1([C:7]2[NH:12][C:11](=[O:13])[CH:10]=[C:9]([C:14]([F:17])([F:16])[F:15])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18]N1C(=O)CCC1=O>C(O)(=O)C>[Br:18][C:10]1[C:11](=[O:13])[NH:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][C:9]=1[C:14]([F:16])([F:17])[F:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1354100074-Hydroxy-2-phenyl-6-(trifluoromethyl)pyrimidine

Product 1

HCID 1358375345-bromo-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinoneYield 83.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.0 g (3.94 mmol) of 2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone and 20 mL of glacial acetic acid was added 1.0 g (5.6 mmol) N-bromosuccinimide and the mixture was left to stir at room temperature for 16 h. The reaction was poured onto ice water and vacuum filtered, washing well with water. The crude product was recrystallized from ethyl acetate to yield 1.05 g (83.5%) of 5-bromo-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone, as a white solid. 1H-NMR (d6DMSO)δ7.6 (3H, m); 8.15 (2H, m).

Workup

  1. waitthe mixture was left
  2. additionThe reaction was poured onto ice water and vacuum
  3. filtrationfiltered
  4. washwashing well with water
  5. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a2589baa386f4cb68df2e82406942c40
Source dataset
uspto-grants-1995_09
Patent number
US05453414

Reaction notes

Loading…