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

HRID 1415685Notes

Reaction equation

HRID 1415685 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:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[S:25][CH:26]=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:26]2[S:25][C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=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 68.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred slurry of aluminum chloride (14.6 g, 110 mmol) in 1,2-dichloroethane at 0° C. was added 4-methoxybenzoylchloride (18.7 g, 110 mmol). The mixture was stirred at 0° C. for ten minutes, and 3-phenylbenzo[b]thiophene (21.0 g, 100 mmol) in 1,2-dichlororethane was added. The mixture was stirred for two hours, with the temperature maintained at 0° C. The reaction mixture was poured into a mixture of ice and hydrochloric acid. The resulting mixture was extracted with ether. The ether extract was washed with water, aqueous sodium bicarbonate, and then again with water. The ether layer was dried over magnesium sulfate and evaporated to dryness. The residue was dissolved in ethanol and kept at 5° C. for three days. The product crystallized out, yielding 23.7 g of the title compound. mp: 94° C.-95° C. EA calculated for C22H16O2S: C, 76.72; H, 4.68; O, 9.29. Found: C, 76.54; H, 4.74; O, 9.25.

Workup

  1. stirringThe mixture was stirred for two hours, with the temperature
  2. temperaturemaintained at 0° C
  3. extractionThe resulting mixture was extracted with ether
  4. extractionThe ether extract
  5. washwas washed with water, aqueous sodium bicarbonate
  6. dry with materialThe ether layer was dried over magnesium sulfate
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in ethanol
  9. customThe product crystallized out

Sources & evidence

ORD record
ord-fccd88f8fe3c4969bae2d3aa1d40eb8e
Source dataset
uspto-grants-1999_06
Patent number
US05908859

Reaction notes

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