Water → 5-Bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole

HRID 1415757Notes

Reaction equation

HRID 1415757 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Br:23]N1C(=O)CCC1=O.O>O1CCCC1>[Br:23][C:12]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 108291321-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole

Product 1

HCID 218628595-Bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrroleYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.32 g (1.0 mmol) of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole (prepared as described in Example 33) was dissolved in 10 ml of anhydrous tetrahydrofuran, and 0.18 g (1.0 mmol) of N-bromosuccinimide was added to the resulting solution, whilst ice-cooling. The mixture was then stirred, whilst ice-cooling for 1 hour and then at room temperature for a further 1 hour. At the end of this time, water was added to the mixture, and the resulting mixture was extracted with methylene chloride. The organic extract was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under reduced pressure. The resulting residue was applied to a silica gel chromatography column and eluted with a 1:3 by volume mixture of ethyl acetate and hexane, to give 0.28 g of the title compound as a white powder (yield 70%), melting at 174-176° C.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. extractionthe resulting mixture was extracted with methylene chloride
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customthe solvent was then removed by distillation under reduced pressure
  7. washeluted with a 1:3 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-711d205d107f4db9aaaf956249b180c1
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

Loading…