1,2-Dichloroethane → Methyl 3-(2-acetylpyrrol-1-yl)benzoate

HRID 399823Notes

Reaction equation

HRID 399823 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].ClCCCl.[N:16]1([C:21]2[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=2)[C:24]([O:26][CH3:27])=[O:25])[CH:20]=[CH:19][CH:18]=[CH:17]1>ClC(Cl)C>[C:1]([C:20]1[N:16]([C:21]2[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=2)[C:24]([O:26][CH3:27])=[O:25])[CH:17]=[CH:18][CH:19]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7918Acetic AnhydrideHCID 3322314Methyl 3-(1H-pyrrol-1-yl)benzoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18945300Methyl 3-(2-acetylpyrrol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Acetic anhydride (1.3 ml) was added to a mixture of aluminum chloride (2.7 g) and 1,2-dichloroethane (10 ml) under ice-cooling and the mixture was stirred for 20 minutes at the same temperature. To the mixture was added dropwise a mixture of methyl 3-(pyrrol-1-yl)benzoate (2.0 g) in dichloroethane (3 ml) for 10 minutes at 0° to 5° C., and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was poured into an ice-water and the mixture was extracted with chloroform. The extract was washed with a saturated aqueous sodium bicarbonate solution and water. The organic layer was dried over magnesium sulfate and evaporated in vacuo to give methyl 3-(2-acetylpyrrol-1-yl)benzoate (0.94 g).

Workup

  1. temperaturecooling
  2. additionTo the mixture was added dropwise
  3. stirringthe mixture was stirred for 3 hours at the same temperature
  4. extractionthe mixture was extracted with chloroform
  5. washThe extract was washed with a saturated aqueous sodium bicarbonate solution and water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6947a8fb2b744587af82371a74b1d2f7
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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