Hydrochloric Acid → 4-Fluoro-2-benzoylthiophenol

HRID 1008751

Reaction equation

HRID 1008751 reaction equation
[S-2:1].[Li+].[Li+].F[C:5]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].Cl.C(OCC)(=O)C>CS(C)=O.O>[F:19][C:16]1[CH:17]=[CH:18][C:5]([SH:1])=[C:6]([C:7](=[O:8])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=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

Conditions

Temperature
120 °C

Procedure

Lithium sulfide (3.5 g) (supplied from Aldrich) was added to a solution of 10.1 g of 2,5-difluorobenzophenone in 200 mL of DMSO, and stirred at 120° C. under a nitrogen atmosphere for 3 hours. Under ice cooling, 200 mL of 1 N hydrochloric acid was added to the reaction solution. Further 400 mL of ethyl acetate and 200 mL of water were added thereto, and the mixture was separated into two liquid phases. The organic layer was washed with 400 mL of water, and then washed with 200 mL of saturated brine. The organic layer was dried on sodium sulfate anhydrate and subsequently concentrated, to yield 10.54 g of the title compound.

Workup

  1. customthe mixture was separated into two liquid phases
  2. washThe organic layer was washed with 400 mL of water
  3. washwashed with 200 mL of saturated brine
  4. customThe organic layer was dried on sodium sulfate anhydrate
  5. concentrationsubsequently concentrated

Sources & evidence

ORD record
ord-e6862eb614de44248cafca7a25714573
Source dataset
uspto-grants-2011_07
Patent number
US07973030B2

Linked notes

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