3-Ethynylbenzoyl chloride → HCID 86634500, compound

HRID 2080922Notes

Reaction equation

HRID 2080922 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[CH:2].[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([S:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])#[CH:2]

Participants

4

Reactant 2

HCID 200388133-Ethynylbenzoyl chlorideHCID 66586497Sodium benzenethiol

Product 1

HCID 86634500HCID 86634500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of m-ethynylbenzoic acid and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50° C. for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride. To the m-ethynylbenzoyl chloride obtained was added 7 ml of THF and the resultant mixture was ice-cooled. Then, 971 mg (7.35 mmol) of sodium benzenethiol was added to the mixture and the resultant mixture was stirred at room temperature for 2 hours. After completion of the stirring, THF was removed by distillation under reduced pressure and 35 ml of water was added to the resultant residue. The mixture was extracted with 35 ml of ethyl acetate, the extract was dried over magnesium sulfate and the solvent was removed by distillation under reduced pressure using an evaporator. The resultant crude reaction product was purified by column chromatography (Hexane/AcOEt=20/1) using silica gel to obtain 0.51 g of S-phenyl 3-ethynyl-thiobenzoate which is a desired product as yellow solid. (Yield: 31%)

Workup

  1. temperaturecooled
  2. customAfter completion of the stirring, THF was removed by distillation under reduced pressure and 35 ml of water
  3. additionwas added to the resultant residue
  4. extractionThe mixture was extracted with 35 ml of ethyl acetate
  5. dry with materialthe extract was dried over magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customan evaporator
  8. customThe resultant crude reaction product
  9. customwas purified by column chromatography (Hexane/AcOEt=20/1)

Sources & evidence

ORD record
ord-862c73b5cecd4d6eb640c817fff56de3
Source dataset
uspto-grants-2011_04
Patent number
US07932398B2

Reaction notes

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