p-Fluoronitrobenzene → HCID 53716539, compound

HRID 2229588Notes

Reaction equation

HRID 2229588 reaction equation
[N:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[OH:9])=[N+:2]=[N-:3].[H-].[Na+].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>CN(C=O)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([O:9][C@@H:5]2[CH2:6][CH2:7][CH2:8][C@H:4]2[N:1]=[N+:2]=[N-:3])=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 13737690HCID 13737690, compound

Product 1

HCID 53716539HCID 53716539, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Trans-1-azidocyclopentan-2-ol 1.27 g was dissolved in DMF and treated with sodium hydride (400 mg. 60%) at room temperature for 1 h. 4-Fluoronitrobenzene (1.41 g) was added and the mixture stirred at 50° C. for 4 h and then left at room temperature overnight. The reaction was quenched with water and extracted with ether. The organic solution was washed with water, dried (MgSO4) and evaporated. Purification by flash chromatography (SiO2-20% DCM/hexane) gave trans-2-(4-nitrophenoxy)cyclopentylazide. 1H nmr (CDCl3) 8.22 (2H, d); 6.98 (2H, d); 5.63 (1H, m); 4.07 (1H, m); 2.20 (2H, m); 1.87 (4H, m).

Workup

  1. waitleft at room temperature overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with ether
  4. washThe organic solution was washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification by flash chromatography (SiO2-20% DCM/hexane)

Sources & evidence

ORD record
ord-5b94bc0a81604cb2bdedfa02bfd0c587
Source dataset
uspto-grants-2002_07
Patent number
US06420438B1

Reaction notes

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