p-Bromobenzenesulfonyl chloride → 1-(4-Bromophenylsulfonyl)-1H-pyrrole

HRID 2239415Notes

Reaction equation

HRID 2239415 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C1COCC1>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8027PyrroleHCID 24758Sodium hydride

Product 1

HCID 51089321-(4-Bromophenylsulfonyl)-1H-pyrroleYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Pyrrole (1.05 mL, 15.0 mmol) was added to a slurry of sodium hydride (0.71 g, 60% in mineral oil, 17.8 mmol) in dry THF (10 mL) at room temperature. 4-Bromobenzene sulfonyl chloride (1.5 g, 6.0 mmol) dissolved in dry THF (5 mL) was added dropwise. The reaction mixture was stirred overnight. The reaction was quenched with saturated ammonium chloride and diluted with ethyl acetate. The layers were separated and the organic layer was washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude product. The crude product was purified via Isco chromatography (the Redisep™ column, silica, gradient 5-50% ethyl acetate in hexane) to give 1-[(4-bromophenyl)sulfonyl]-1H-pyrrole (0.27 g, 16%). MS (ESI) m/z 286. HPLC purity 100.0% at 210-370 nm, 9.9 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

Workup

  1. additionwas added dropwise
  2. customThe reaction was quenched with saturated ammonium chloride
  3. additiondiluted with ethyl acetate
  4. customThe layers were separated
  5. washthe organic layer was washed with water and brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude product
  10. customThe crude product was purified via Isco chromatography (the Redisep™ column, silica, gradient 5-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-dc9ef1013d3744269deffb6d5689919a
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

Loading…