Pyrrole → HCID 23441042, compound

HRID 2119364Notes

Reaction equation

HRID 2119364 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[Br:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C1COCC1.[Cl-].[Na+].O>[Br:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([N:3]2[CH:7]=[CH:6][CH:5]=[CH:4]2)(=[O:18])=[O:17])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 8027PyrroleHCID 24758Sodium hydrideHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 23441042HCID 23441042, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

NaH (60% dispersion in mineral oil. 40 mg, 1.0 mmol) was added to a solution of pyrrole (67 mg, 1.0 mmol) in THF (2.0 mL) and the mixture was stirred at room temperature for 5 min. Then 4-(bromomethyl)benzenesulfonyl chloride (269 mg, 1.0 mmol) was added to the mixture. After stirring at room temperature for additional 10 min, brine (15 mL) was added and the mixture was extracted with AcOEt (40 mL×2). The combined extracts were dried over MgSO4. The solvent was removed under reduced pressure to afford an oil which was purified by column chromatography (SiO2, 10% AcOEt/hexane) to give 1-[4-(bromomethyl)benzenesulfonyl]pyrrole: 46 mg, 15% yield, colorless oil. The purity was determined by GC/MS (>95%), m/e 299 (M+, C11H10NO2BrS).

Workup

  1. stirringAfter stirring at room temperature for additional 10 min
  2. extractionthe mixture was extracted with AcOEt (40 mL×2)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto afford an oil which
  6. customwas purified by column chromatography (SiO2, 10% AcOEt/hexane)

Sources & evidence

ORD record
ord-e796be7c17c74af38f9a5eec2582da46
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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