Ethyl Acetate → 3-(2,4-Dichlorobenzoyl)-5-(methoxycarbonyl)-2-methylbenzo[b]thiophene

HRID 1699851Notes

Reaction equation

HRID 1699851 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[CH3:16][O:17][C:18]([C:20]1[CH:29]=[CH:28][C:23]2[S:24][C:25]([CH3:27])=[CH:26][C:22]=2[CH:21]=1)=[O:19].C(OCC)(=O)C>C(Cl)Cl>[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8]([C:26]1[C:22]2[CH:21]=[C:20]([C:18]([O:17][CH3:16])=[O:19])[CH:29]=[CH:28][C:23]=2[S:24][C:25]=1[CH3:27])=[O:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 666452,4-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 136630372-Methylbenzo[b]thiophene-5-carboxylic acid methyl ester

Product 1

HCID 223877633-(2,4-Dichlorobenzoyl)-5-(methoxycarbonyl)-2-methylbenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum chloride (1.24 g, 9.3 mmol) was dispersed in methylene chloride (10 ml), and 2,4-dichlorobenzoyl chloride (0.97 g, 4.7 mmol) and then 5-(methoxycarbonyl)-2-methylbenzo[b]thiophene(0.8 g, 3.9 mml) were added thereto. The mixture was stirred at room temperature for 4 hr. The reaction mixture was poured into ice water and ethyl acetate was added. The mixture was extracted. The organic layer was washed twice with a saturated aqueous solution of sodium hydrogencarbonate and once with brine, and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure to give the objective compound (1.5 g, quantitative) as pale yellow crystals.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted
  3. washThe organic layer was washed twice with a saturated aqueous solution of sodium hydrogencarbonate and once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto give the objective compound (1.5 g, quantitative) as pale yellow crystals

Sources & evidence

ORD record
ord-88cfcc75b957439d93fd1b3606f0a701
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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