Boron trifluoride → 1-Benzenesulfonyl-2-(4-fluorobenzoyl)pyrrole

HRID 1167978

Reaction equation

HRID 1167978 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.B(F)(F)F.[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>ClCCl>[C:15]1([S:21]([N:24]2[CH:25]=[CH:26][CH:27]=[C:28]2[C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:23])=[O:22])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 678794-Fluorobenzoyl chlorideHCID 1401461-Phenylsulfonylpyrrole

Product 1

HCID 219729051-Benzenesulfonyl-2-(4-fluorobenzoyl)pyrroleYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 4-fluorobenzoylchloride (1.74 g, 11 mmol) in dichloromethane (2 ml) was added dropwise a solution of boron trifluoride diethyletherate (3.4 ml, 27.6 mmol) in dichloromethane (20 ml). The mixture was stirred for 10 minutes at room temperature. Subsequently, to the mixture was added dropwise a solution of 1-benzenesulfonylpyrrole (1.9 g, 9.2 mmol) in accordance with a method described in Example 8 (1) in dichloromethane (5 ml). The mixture was stirred for 12 hours. The reaction mixture was poured into ice-water and extracted with ethylacetate. The extract was washed with water and dried. The solvent was evaporated. The obtained crude crystal was recrystallized from isopropylether to give 1-benzenesulfonyl-2-(4-fluorobenzoyl)pyrrole (1.0 g) as a crystal. Yield: 19.8%.

Workup

  1. stirringThe mixture was stirred for 12 hours
  2. extractionextracted with ethylacetate
  3. washThe extract was washed with water
  4. customdried
  5. customThe solvent was evaporated
  6. customThe obtained crude crystal
  7. customwas recrystallized from isopropylether

Sources & evidence

ORD record
ord-417490e6bfb1404886152f4839f0b2be
Source dataset
uspto-grants-2003_09
Patent number
US06620841B1

Linked notes

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