Phenylacetyl chloride → HCID 21802476, compound

HRID 924972Notes

Reaction equation

HRID 924972 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:15]1([S:21]([N:24]2[CH:28]=[CH:27][CH:26]=[CH:25]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCOC(C)=O>ClCCCl>[C:1]1([CH2:7][C:8]([C:26]2[CH:27]=[CH:28][N:24]([S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:23])=[O:22])[CH:25]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8857Ethyl AcetateHCID 1401461-PhenylsulfonylpyrroleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21802476HCID 21802476, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under N2, a mixture of phenyl-acetyl chloride (1.5 g, 9.7 mmol) in 1,2-dichloro-ethane (20 mL) was added AlCl3 (2.24 g, 16.8 mmol) and then stirred at room temperature for 15 minutes. 1-(phenylsulfonyl)-1H-pyrrole (1.74 g, 8.4 mmol) was added. The mixture was stirred at room temperature overnight, followed by a standard aqueous/EtOAc workup. Purified by column chromatography to afford the Intermediate 52 (1.4 g, yield 51.8%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customPurified by column chromatography

Sources & evidence

ORD record
ord-838c372c9ef74e10a91c1d246212ff12
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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