Bromine → HCID 178517592, compound

HRID 1739647Notes

Reaction equation

HRID 1739647 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:4]([OH:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[Br:12]Br>CO>[F:11][C:2]([F:1])([F:10])[C:3]1[C:4]([OH:9])=[N:5][CH:6]=[C:7]([Br:12])[CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 36784112(1H)-Pyridinone, 3-(trifluoromethyl)-

Product 1

HCID 178517592HCID 178517592, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Trifluoromethyl-2-pyridinol (5.0 g, 0.031 mol) was dissolved with stirring in methanol (75 mL) and bromine (5.25 g, 0.033 mol) was added dropwise with cooling. The mixture was stirred overnight and evaporated to dryness. The residue was dissolved in ethyl acetate (250 mL), washed twice with water and brine, dried over sodium sulphate and evaporated to dryness. Chromatography over silica (20% ethyl acetate:80% hexane) gave 3-trifluoromethyl-5-bromo-2-pyridinol (5.2 g) as a cream solid. M.P. 160-162° C.

Workup

  1. temperaturewith cooling
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate (250 mL)
  4. washwashed twice with water and brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-fb4997991f87444aaec5d699703d70b0
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

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