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

HRID 1463236

Reaction equation

HRID 1463236 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-162b3bb29c6d475dbb62223325d6bf4c
Source dataset
uspto-grants-1994_04
Patent number
US05300477

Linked notes

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