Hydrochloric Acid → 2-(4-Methoxybenzoyl)-3-phenylbenzothiophene

HRID 616625Notes

Reaction equation

HRID 616625 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[C:16]1([C:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[S:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>ClCCCl>[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([C:23]2[S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:22]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 6108813-PhenylbenzothiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 154064042-(4-Methoxybenzoyl)-3-phenylbenzothiopheneYield 70%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred slurry of 14.6 g. (0.11 mole) of aluminum chloride in 1,2-dichloroethane maintained at 0° C. were added 18.7 g. (0.11 mole) of 4-methoxybenzoyl chloride. The mixture was stirred at 0° C. for 10 minutes, and 21.0 g. (0.1 mole) of 3-phenylbenzothiophene in 1,2-dichloroethane were added. The mixture was stirred for two hours, the temperature being maintained at 0° C. The reaction mixture then was poured into a mixture of hydrochloric acid in ice. The resulting mixture was extracted with ether. The ether extract was washed with water, dilute aqueous sodium bicarbonate, and water. The ether layer was dried over magnesium sulfate, and the ether solvent was evaporated. The residue was dissolved in ethanol. The ethanol solution was filtered and maintained at 5° C. for three days. The resulting crystals were filtered and washed with ethanol and petroleum ether to obtain 23.7 g. (70 percent) of the title compound, m.p. 94°-95° C. The nmr spectrum was consistent with the structure of the title compound.

Workup

  1. additionwere added 18.7 g
  2. stirringThe mixture was stirred for two hours
  3. temperaturethe temperature being maintained at 0° C
  4. extractionThe resulting mixture was extracted with ether
  5. extractionThe ether extract
  6. washwas washed with water, dilute aqueous sodium bicarbonate, and water
  7. dry with materialThe ether layer was dried over magnesium sulfate
  8. customthe ether solvent was evaporated
  9. dissolutionThe residue was dissolved in ethanol
  10. filtrationThe ethanol solution was filtered
  11. temperaturemaintained at 5° C. for three days
  12. filtrationThe resulting crystals were filtered
  13. washwashed with ethanol and petroleum ether
  14. customto obtain 23.7 g

Sources & evidence

ORD record
ord-f9b5cfe1d38646e5adb4ff9b026cc383
Source dataset
uspto-grants-1978_02
Patent number
US04075227

Reaction notes

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