Hydrochloric Acid → Methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate

HRID 399824Notes

Reaction equation

HRID 399824 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[N:8]1([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9]1.N1C=CC=CC=1.Cl>ClCCCl.O.C(Cl)(Cl)Cl>[Cl:1][C:2]([Cl:7])([Cl:6])[C:3]([C:12]1[N:8]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 3322314Methyl 3-(1H-pyrrol-1-yl)benzoate

Product 1

HCID 18945198Methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Trichloroacetyl chloride (15.5 ml) was added to a mixture of methyl 3-(pyrrol-1-yl)benzoate (14.0 g) and pyridine (16.9 ml) in 1,2-dichloroethane (70 ml) under ice-cooling and the mixture was stirred for 7 days at ambient temperature. The mixture was poured into a mixture of chloroform and water, and the mixture was adjusted to pH 1 with 6N-hydrochloric acid. The separated organic layer was washed with a saturated aqueous sodium bicarbonate solution and water. The mixture was dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate (21.23 g).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with a saturated aqueous sodium bicarbonate solution and water
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-8bfe52f7eaf74760a8571bf51d2959ac
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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