Acetyl chloride → 1-(3-Phenylthiophen-2-yl)ethanone

HRID 2267399Notes

Reaction equation

HRID 2267399 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](Cl)(=[O:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:1]1([C:7]2[CH:11]=[CH:10][S:9][C:8]=2[C:12](=[O:14])[CH3:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([C:7]2[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[S:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 754733-PhenylthiopheneHCID 6451240Aluminum(III) Chloride

Product 2

HCID 9015411-(3-Phenylthiophen-2-yl)ethanoneYield 41%HCID 135416931-(4-Phenylthiophen-2-yl)ethan-1-oneYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-phenylthiophene (3.10 g, 19.3 mmol) and acetyl chloride (1.38 mL, 23.2 mmol) in dichloromethane (50 mL) was cooled to 0° C. Aluminium (III) chloride (2.58 g, 19.3 mmol) was added in several portions to control an otherwise vigorous exotherm. After addition was complete, the bath was removed and the reaction allowed to stir at ambient temperature for 2 h. The reaction mixture was then diluted with saturated aqueous NaHCO3 and the layers were separated. The organic phase was washed with another portion of NaHCO3 solution and brine. The resulting dichloromethane solution was concentrated in vacuo and the residue was purified by flash chromatography eluting with a gradient of 1-5% EtOAc/hexanes to afford 1.62 g (41% yield) of 1-(3-phenylthiophen-2-yl)ethanone and 1.13 g (29% yield) of 1-(4-phenylthiophen-2-yl)ethanone which were both spectroscpopically identical to literature compounds (See reference: Acta Chemica Scandinavica (1947-1973) 1970, 24, pp. 99-104.)

Workup

  1. additionAfter addition
  2. customthe bath was removed
  3. additionThe reaction mixture was then diluted with saturated aqueous NaHCO3
  4. customthe layers were separated
  5. washThe organic phase was washed with another portion of NaHCO3 solution and brine
  6. concentrationThe resulting dichloromethane solution was concentrated in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with a gradient of 1-5% EtOAc/hexanes

Sources & evidence

ORD record
ord-82af840b72f44d509b0062b7fd75c206
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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