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

HRID 1267936Notes

Reaction equation

HRID 1267936 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-a079b78735e7419c86821e4321cad618
Source dataset
uspto-grants-2003_04
Patent number
US06555557B1

Reaction notes

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