p-Fluoronitrobenzene → HCID 53716539, compound

HRID 1384894Notes

Reaction equation

HRID 1384894 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 1h. 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-fa3492455d2f43208c3a73ae4cd8f226
Source dataset
uspto-grants-2001_07
Patent number
US06262069B1

Reaction notes

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