Boron trifluoride etherate → (1-benzenesulfonyl-1H-pyrrol-2-yl)(4-methylphenyl)ketone

HRID 1352842Notes

Reaction equation

HRID 1352842 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([CH3:24])[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=1.B(F)(F)F.CCOCC>ClCCl>[C:1]1([S:7]([N:10]2[CH:11]=[CH:12][CH:13]=[C:14]2[C:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:24])=[CH:16][CH:17]=2)=[O:22])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 134054-Methylbenzoyl ChlorideHCID 1401461-Phenylsulfonylpyrrole

Product 1

HCID 22928710(1-benzenesulfonyl-1H-pyrrol-2-yl)(4-methylphenyl)ketoneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 1-benzenesulfonyl-1H-pyrrole (284 g, 1.37 mol) in dichloromethane (1.0 L) were added p-toluoyl chloride (318 g, 2.06 mol) and boron trifluoride-diethyl ether (350 g, 2.47 mol) under an atmosphere of nitrogen. The mixture was allowed to stand at room temperature for 7 days. The reaction solution was washed with 1N hydrochloric acid (750 ml) twice, an aqueous 1N sodium hydroxide solution (750 ml) and a saturated aqueous sodium chloride solution (100 ml) in the order, dried and filtered. The filtrate was further concentrated to about 500 ml at atmospheric pressure, followed by addition of hexane (500 ml). Further the solution was concentrated to about 500 ml and cooled to 10° C. The precipitate was filtered, washed with hexane and toluene in the order, and dried to give the subject compound (315 g, 71%).

Workup

  1. washThe reaction solution was washed with 1N hydrochloric acid (750 ml) twice
  2. dry with materialan aqueous 1N sodium hydroxide solution (750 ml) and a saturated aqueous sodium chloride solution (100 ml) in the order, dried
  3. filtrationfiltered
  4. concentrationThe filtrate was further concentrated to about 500 ml at atmospheric pressure
  5. additionfollowed by addition of hexane (500 ml)
  6. concentrationFurther the solution was concentrated to about 500 ml
  7. filtrationThe precipitate was filtered
  8. washwashed with hexane and toluene in the order
  9. customdried

Sources & evidence

ORD record
ord-f137ab93d1c54cc68ad8d703e82210e2
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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