4-Fluorobenzenesulfonyl chloride → 1-(4-Fluorobenzenesulfonyl)pyrrolidine

HRID 743871

Reaction equation

HRID 743871 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>O>[N:1]1([S:13]([C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=2)(=[O:15])=[O:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 7965781-(4-Fluorobenzenesulfonyl)pyrrolidineYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of pyrolidine (17 mL, 237 mmol) in 20 mL of H2O at room temperature was added p-flourobenzenesulfonyl chloride (15 g, 79 mmol) in portions over a 5 minute period. After 1 hour, the solution was diluted with 100 mL of H2O and extracted with ethyl acetate (3×50 mL). The organic was dried Na2SO4) and concentrated in vacuo to give 12.3 g (72%) of 4-(pyrrolidinosulfonyl)flourobenzene as a colorless oil that solidified on standing. This material was used in the following reaction without further purification. MS.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1651f2cc1b841ffbb099b09110f4174
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Linked notes

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