Hydrochloric Acid → 4-Fluoro-2-benzoylthiophenol

HRID 970305Notes

Reaction equation

HRID 970305 reaction equation
F[C:2]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[S-2:17].[Li+].[Li+].Cl.C(OCC)(=O)C>CS(C)=O.O>[F:16][C:13]1[CH:14]=[CH:15][C:2]([SH:17])=[C:3]([C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 5228262,5-DifluorobenzophenoneHCID 10290727Dilithium Sulfide

Product 1

HCID 230742324-Fluoro-2-benzoylthiophenolYield 98%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 10.1 g of 2,5-difluorobenzophenone in 200 ml of DMSO was added 3.5 g of lithium sulfide (manufactured by ALDRICH CHEMICAL COMPANY) and the mixture was stirred in a nitrogen atmosphere at 1200C for 3 hours. To the reaction solution was added 200 ml of 1N hydrochloric acid under ice cooling, and further 400 ml of ethyl acetate and 200 ml of water were added to the mixture to separate it. The organic layer was washed with 400 ml of water and then with 200 ml of saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 10.54 g of the title compound.

Workup

  1. customto separate it
  2. washThe organic layer was washed with 400 ml of water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6aaa1581e5f04015a3162ff4b7427b83
Source dataset
uspto-grants-2007_12
Patent number
US07312208B2

Reaction notes

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