Acetone → 2-[(3-Bromophenyl)thio]-3-pyridinol

HRID 1841541Notes

Reaction equation

HRID 1841541 reaction equation
Br[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([SH:16])[CH:13]=[CH:14][CH:15]=1.CC(C)=O.C(OCC)(=O)C>O1CCCC1>[Br:9][C:10]1[CH:11]=[C:12]([S:16][C:2]2[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 180Acetone2×HCID 8857Ethyl AcetateHCID 230702-Bromo-3-pyridinolHCID 80597m-Bromobenzenethiol

Product 1

HCID 114602232-[(3-Bromophenyl)thio]-3-pyridinolYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Bromo3-pyridinol (44 g, 250 mmol) and 3-bromothiophenol (30 g, 160 mmol) are dissolved in tetrahydrofuran (hereinafter, occasionally referred to as THF) (100 ml) and dimethylformaldehyde (hereinafter, referred to as DMF) (100 ml), and the mixture is heated under reflux for 5 hours. After being allowed to cool, ethyl acetate (1000 ml) is added to the mixture, and the mixture is washed with 5% aqueous sodium hydroxide solution (50 ml×2) and a saturated brine (100 ml×2), and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate to give the title compound (35 g) as colorless crystals, m.p. 125-126° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5 hours
  3. temperatureto cool
  4. washthe mixture is washed with 5% aqueous sodium hydroxide solution (50 ml×2)
  5. dry with materiala saturated brine (100 ml×2), and dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9ba748b1e7fe49259861f52110ea293e
Source dataset
uspto-grants-2004_01
Patent number
US06683186B2

Reaction notes

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