Lawesson's reagent → 6-Chloro-5-hydroxy-2,2-dimethyl-benzofurane-3-thione

HRID 1871847Notes

Reaction equation

HRID 1871847 reaction equation
[Cl:1][C:2]1[C:13]([OH:14])=[CH:12][C:5]2[C:6](=O)[C:7]([CH3:10])([CH3:9])[O:8][C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:13]([OH:14])=[CH:12][C:5]2[C:6](=[S:24])[C:7]([CH3:10])([CH3:9])[O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 186893816-Chloro-5-hydroxy-2,2-dimethyl-benzofuran-3-one

Product 1

HCID 186893806-Chloro-5-hydroxy-2,2-dimethyl-benzofurane-3-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 20 mmol 6-chloro-5-hydroxy-2,2-dimethyl-benzofuran-3-one in 30 ml toluene is admixed with 10 mmol Lawesson's reagent and heated for 3 hours to boiling under reflux. After cooling to room temperature it is filtered on 50 g silica gel. The red fraction of the filtrate is collected. After removing the toluene by distillation a red oil remains.

Workup

  1. temperatureheated for 3 hours
  2. temperatureunder reflux
  3. filtrationis filtered on 50 g silica gel
  4. customThe red fraction of the filtrate is collected
  5. customAfter removing the toluene
  6. distillationby distillation a red oil

Sources & evidence

ORD record
ord-4c13c2748a604d56b4981abffdcbb31d
Source dataset
uspto-grants-2000_08
Patent number
US06107036

Reaction notes

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