Bromine → HCID 178517749, compound

HRID 132838Notes

Reaction equation

HRID 132838 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([OH:9])=[N: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 517045Sodium AcetateHCID 178516044HCID 178516044, compound

Product 1

HCID 178517749HCID 178517749, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-trifluoromethyl-2-pyridinol (51 g, 310 mmol) and sodium acetate (26.2 g, 319 mmol) in glacial acetic acid (200 mL) was added bromine (16.7 mL, 325 mmol) and the resultant mixture was heated at 80° C. for 2.5 h. The reaction was allowed to cool to room temperature and then was evaporated under reduced pressure. The residue was neutralized with saturated aqueous sodium bicarbonate solution and extracted with 3 portions of ethyl acetate. The organic extracts were combined, dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 8.04 (d, J=2.6 Hz, 1H), 7.89 (m, 1H).

Workup

  1. customwas evaporated under reduced pressure
  2. extractionextracted with 3 portions of ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-763f874e9c564375ab8eee20fcab0496
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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