N-bromobutanimide → HCID 10053229, compound

HRID 1906495Notes

Reaction equation

HRID 1906495 reaction equation
[C:1]1([CH3:32])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[C:11]2[C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Br:33]N1C(=O)CCC1=O>O1CCCC1.O>[C:1]1([CH3:32])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[C:11]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:24][CH:23]=3)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:13]=[C:14]2[Br:33])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13799845HCID 13799845, compound

Product 1

HCID 10053229HCID 10053229, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-toluenesulfonyl)-2-(4-methylsulfonylphenyl)-3-(4-fluorophenyl)pyrrole (10.0 g, 0.021 mole) in 100 ml tetrahydrofuran was cooled in an ice bath and treated with N-bromosuccinimide (3.8 g, 0.021 mole) and stirred for five hours. The mixture was diluted with one liter of water and the resulting solid was collected by filtration, washed with water and dried. The crude product was recrystallized from ethyl acetate/hexane to yield 10.0 g (87% yield); m.p. 207°-207.5°.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried
  4. customThe crude product was recrystallized from ethyl acetate/hexane
  5. customto yield 10.0 g (87% yield)

Sources & evidence

ORD record
ord-5e062f1b7dab4ee295551eb1c4d10fbf
Source dataset
uspto-grants-1987_03
Patent number
US04652582

Reaction notes

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