2,4-Dichlorobenzoyl chloride → HCID 22388405, compound

HRID 1072813Notes

Reaction equation

HRID 1072813 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[O:24][C:25]([CH3:27])=[CH:26][C:22]=2[CH:21]=1)=[O:19]>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[O:24][C:25]=1[CH3:27])=[O:9]

Participants

5

Reactant 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22387841HCID 22387841, compound

Product 1

HCID 22388405HCID 22388405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum chloride (2.52 g, 18.9 mmol) was suspended in methylene chloride (25 ml) and 2,4-dichlorobenzoyl chloride (1.98 g, 9.5 mmol) was added. Then, 5-(methoxycarbonyl)-2-methylbenzo[b]furan (1.5 g, 7.9 mmol) was added and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (twice) and then saturated 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 (2.9 g, quantitative) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (twice) and then saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give the objective compound (2.9 g, quantitative) as colorless crystals

Sources & evidence

ORD record
ord-bbf1cc2b52d24c94a0a2696c00bf5957
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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