Reaction #11333

Reaction equation

4-fluorobenzoylchloride

boron trifluoride

1-benzenesulfonylpyrrole

→

1-benzenesulfonyl-2-(4-fluorobenzoyl)pyrrole

Yield 33.0%

Solvents

dichloromethane

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was stirred for 12 hours
2. 2
   Extractionextracted with ethylacetate
3. 3
   WashThe extract was washed with water
4. 4
   Otherdried
5. 5
   OtherThe solvent was evaporated
6. 6
   OtherThe obtained crude crystal
7. 7
   Otherwas recrystallized from isopropylether

Procedure

To a solution of 4-fluorobenzoylchloride (1.74 g, 11 mmol) in dichloromethane (2ml) 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.

Source