p-Fluoronitrobenzene → HCID 22341962, compound

HRID 583724Notes

Reaction equation

HRID 583724 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH:6]1[CH2:10][CH2:9][CH2:8][NH:7]1.C(=O)([O-])[O-].[K+].[K+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>O>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([N:1]2[CH2:5][CH2:4][CH2:3][CH:2]2[CH:6]2[CH2:10][CH2:9][CH2:8][N:7]2[C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 142110792,2′-Bipyrrolidine

Product 1

HCID 22341962HCID 22341962, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.6 g (˜15 mmol) of [2,2′]bipyrrolidinyl (1) obtained above were refluxed in the presence of 5 g (35.7 mmol) of potassium carbonate and 5 g (35.7 mmol) of para-fluoronitrobenzene in 25 ml of water overnight. The agglomerate formed was filtered off and then rinsed with acetone and isopropanol to give 2.15 g of a mixture of two isomers (55/45) (44%). After purification by chromatography on silica gel, a majority isomer was isolated (1.2 g), the analyses for which were:

Workup

  1. customThe agglomerate formed
  2. filtrationwas filtered off
  3. washrinsed with acetone and isopropanol

Sources & evidence

ORD record
ord-13bf8d75c3344c1586ff608ae273d709
Source dataset
uspto-grants-2005_08
Patent number
US06923835B2

Reaction notes

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