Nitronium tetrafluoroborate → HCID 22506991, compound

HRID 985459Notes

Reaction equation

HRID 985459 reaction equation
NC1N=C(OC2C3C(=CC=CC=3)C(NC(N[C:23]3[CH:28]=[C:27]([C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])[CH:26]=[CH:25][C:24]=3[O:36][CH3:37])=O)=CC=2)C=CN=1.F[B-](F)(F)F.[O:43]=[N+:44]=[O:45]>C(#N)C>[N+:44]([C:25]1[CH:26]=[C:27]([C:29]([F:34])([F:35])[C:30]([F:33])([F:32])[F:31])[CH:28]=[CH:23][C:24]=1[O:36][CH3:37])([O-:45])=[O:43]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 11663591HCID 11663591, compound

Product 1

HCID 22506991HCID 22506991, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above 4-pentafluoroethylanisole (1.131 g, 0.005 mol) was combined with 10 mL acetonitrile in a 3-neck micro flask. Nitronium tetrafluoroborate (0/797 g, 0.006 mol) was added in portions causing the clear solution to turn brown. The reaction was stirred overnight at room temperature, concentrated, and the product purified by Kugelrohr distillation. The desired 2-nitro-4-pentafluoroethylanisole (0.8 g, bp>80° C.) was obtained as a slightly yellow oil that formed a semi-solid after sitting 60 h.

Workup

  1. concentrationconcentrated
  2. distillationthe product purified by Kugelrohr distillation

Sources & evidence

ORD record
ord-cca21aa74b2d4c508e8dc59632fa1d6c
Source dataset
uspto-grants-2005_03
Patent number
US06872726B2

Reaction notes

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