1-(5-Bromo-4-chlorothiophen-2-yl)ethan-1-one → 2-Acetyl-4-chlorothiophene

HRID 2362262Notes

Reaction equation

HRID 2362262 reaction equation
Br[C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[Cl:10].C(O[Na])(C)=O>CCO.[Pd]>[Cl:10][C:3]1[CH:4]=[C:5]([C:7](=[O:9])[CH3:8])[S:6][CH:2]=1

Participants

5

Reactant 2

HCID 469118821-(5-Bromo-4-chlorothiophen-2-yl)ethan-1-oneHCID 178418247HCID 178418247, compound

Product 1

HCID 111056552-Acetyl-4-chlorothiopheneYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 28-2 (3.20 mg, 13.36 mmol) in EtOH (70 mL) was added 10% Pd/C (2.50 g) and AcONa (1.10 g, 13.36 mmol). The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 3 h, filtered, and the filtrate was concentrated. The resultant residue was dissolved in EA (100 mL) washed with sat. NaHCO3 (40 mL) and brine (30 mL), dried over anhydrous Na2SO4, filtered, concentrated and purified by silica gel column chromatography (PE/EA=30/1 to 5/1) to afford 28-3 as a yellow oil (1.32 g, yield: 62%).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe resultant residue was dissolved in EA (100 mL)
  4. washwashed with sat. NaHCO3 (40 mL) and brine (30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (PE/EA=30/1 to 5/1)

Sources & evidence

ORD record
ord-4add9cbc1b43441ebf6b11ba65d1bfae
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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