3-Chloropropionyl chloride → 3-Chloro-1-(5-fluoro-3-methylbenzo[b]thiophen-2-yl)propan-1-one

HRID 2229259Notes

Reaction equation

HRID 2229259 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][CH:7]=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[Cl:12][CH2:13][CH2:14][C:15](Cl)=[O:16].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S.C(OCC)(=O)C>[Cl:12][CH2:13][CH2:14][C:15]([C:7]1[S:6][C:5]2[CH:10]=[CH:11][C:2]([F:1])=[CH:3][C:4]=2[C:8]=1[CH3:9])=[O:16]

Participants

6

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 5968285-Fluoro-3-methyl-benzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 184670213-Chloro-1-(5-fluoro-3-methylbenzo[b]thiophen-2-yl)propan-1-one

Reagents, catalysts & solvents 2

HCID 6348Carbon DisulfideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-fluoro-3-methylbenzo[b]thiophene (9.97 g) and 3-chloropropionyl chloride (7.45 ml) in carbon disulfide (100 ml) was added AlCl3 (16.00 g) at 0° C. The mixture was stirred at room temperature for 2 hours, poured onto crushed ice, and diluted with ethyl acetate. The extract was washed with 1N HCl, water and brine, dried over MgSO4, and concentrated. The residue was washed with ethanol and hexane to give the titled compound as colorless crystals (12.75 g).

Workup

  1. additionpoured
  2. customonto crushed ice
  3. washThe extract was washed with 1N HCl, water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. washThe residue was washed with ethanol and hexane

Sources & evidence

ORD record
ord-387724cbd5bb4aa59e6bea4dc0720116
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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