Bromine → HCID 178517749, compound

HRID 1976050Notes

Reaction equation

HRID 1976050 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6](=[O:9])[NH:7][CH:8]=1.C([O-])(=O)C.[Na+].[Br:17]Br>C(O)(=O)C>[Br:17][C:5]1[C:6]([OH:9])=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 1474432-Hydroxy-5-(trifluoromethyl)pyridineHCID 517045Sodium Acetate

Product 1

HCID 178517749HCID 178517749, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

5-Trifluoromethyl-2(1H)-pyridone (10.0 g) and sodium acetate (5.25 g, 64 mmol) in acetic acid (100 ml) was treated with bromine (3.3 ml, 63 mmol) and heated at 80° C. for 2 hrs, before being cooled and concentrated. The residue was basified with sodium hydrogen carbonate solution (250 ml) and extracted with ethyl acetate (2×250 ml). The extracts were dried (MgSO4) and concentrated to give the product as a tan solid (14.22 g, 96% yield).

Workup

  1. temperaturebefore being cooled
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (2×250 ml)
  4. dry with materialThe extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-216c0e643fdf4bad93cd9731b1c176a2
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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