4-Phenylbenzoyl chloride → HCID 22387999, compound

HRID 1072820Notes

Reaction equation

HRID 1072820 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([C:11]2[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:20][O:21][C:22]([C:24]1[CH:33]=[CH:32][C:27]2[O:28][C:29]([CH3:31])=[CH:30][C:26]=2[CH:25]=1)=[O:23]>C(Cl)Cl>[CH3:20][O:21][C:22]([C:24]1[CH:33]=[CH:32][C:27]2[O:28][C:29]([CH3:31])=[C:30]([C:15](=[O:16])[C:14]3[CH:18]=[CH:19][C:11]([C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:12][CH:13]=3)[C:26]=2[CH:25]=1)=[O:23]

Participants

5

Reactant 3

HCID 841514-Phenylbenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22387841HCID 22387841, compound

Product 1

HCID 22387999HCID 22387999, compoundYield 118.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aluminum chloride (0.80 g) was stirred in methylene chloride (10 ml) at room temperature. Thereto was added 4-phenylbenzoyl chloride (0.67 g), and then a solution of 5-(methoxycarbonyl)-2-methylbenzo[b]furan (0.67 g) in methylene chloride (5 ml), and the mixture was stirred for 4 hr. Ice was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogencarbonate (twice) and saturated brine (once), dried over sodium sulfate and concentrated to give the objective compound (1.36 g).

Workup

  1. additionIce was added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate (twice) and saturated brine (once),
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5aafd33305a4ad586e0c67916404cb3
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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