Water → (2,5-Dichlorophenyl)[4-(1H-pyrrol-1-yl)phenyl]methanone

HRID 1946223Notes

Reaction equation

HRID 1946223 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9](F)=[CH:8][CH:7]=1)=[O:5].[NH:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:18]2[CH:22]=[CH:21][CH:20]=[CH:19]2)=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8027PyrroleHCID 11430Potassium CarbonateHCID 120399992,5-dichloro-4'-fluorobenzophenon

Product 1

HCID 59165206(2,5-Dichlorophenyl)[4-(1H-pyrrol-1-yl)phenyl]methanoneYield 79.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A charge of 134.6 g (0.500 mol) of 2,5-dichloro-4′-fluorobenzophenone, 50.3 g (0.750 mol) of pyrrole, 76.0 g (0.550 mol) of potassium carbonate and 840 mL of dehydrated N,N′-dimethylacetamide was weighed into a 2-L three-neck flask equipped with a stirrer, a thermometer, a cooling tube and a nitrogen gas introducing tube. The reaction solution was heated under nitrogen atmosphere to 100° C. for 3 hours using an oil bath. After the disappearance of raw materials was confirmed by thin layer chromatography, the reaction solution was left to cool to room temperature. The reaction solution was then gradually added to 3 L of water to coagulate a product, which was filtered. The product obtained by filtration was dissolved in 2.5 L of toluene, which was washed with brine using a separating funnel until an aqueous layer became neutral. After the organic layer was dried over magnesium sulfate, the solvent was removed by an evaporator. A crude yield was 133.3 g. A mixed solvent of hexane and ethyl acetate was used for recrystallization to yield 125.3 g (0.396 mol) of a purified product targeted in 79.3% yield.

Workup

  1. customwas weighed into a 2-L three-neck flask
  2. customequipped with a stirrer
  3. additiona thermometer, a cooling tube and a nitrogen gas introducing tube
  4. waitthe reaction solution was left
  5. temperatureto cool to room temperature
  6. filtrationwas filtered
  7. customThe product obtained by filtration
  8. washwhich was washed with brine using a separating funnel until an aqueous layer
  9. dry with materialAfter the organic layer was dried over magnesium sulfate
  10. customthe solvent was removed by an evaporator
  11. customA mixed solvent of hexane and ethyl acetate was used for recrystallization

Sources & evidence

ORD record
ord-d2d8bdce13c24179993913c7458df306
Source dataset
uspto-grants-2013_03
Patent number
US08399148B2

Reaction notes

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