Trifluoroacetic anhydride → 2-Cyano-4,5-dimethoxy-3-(2,2,2-trifluoroethoxy)nitrobenzene

HRID 2228522Notes

Reaction equation

HRID 2228522 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[NH4+].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:19][O:20][C:21]1[C:22]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:24]#[N:25]>ClCCl>[C:24]([C:23]1[C:22]([O:31][CH2:32][C:33]([F:34])([F:35])[F:36])=[C:21]([O:20][CH3:19])[C:28]([O:29][CH3:30])=[CH:27][C:26]=1[N+:1]([O-:4])=[O:2])#[N:25]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 22985Ammonium nitrateHCID 184706363,4-Dimethoxy-2-(2,2,2,-trifluoroethoxy)benzonitrile

Product 1

HCID 184706192-Cyano-4,5-dimethoxy-3-(2,2,2-trifluoroethoxy)nitrobenzeneYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ammonium nitrate (2.82 g, 0.035 mol) and trifluoroacetic anhydride (12.4 ml, 0.088 mol) were added to a solution of 3,4-dimethoxy-2-(2,2,2,-trifluorethoxy)benzonitrile in dichloromethane. The temperature was maintained between 20° C. and 30° C. for 2 hours, after which time the reaction mixture was washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried (MgSO4) and evaporated under reduced pressure. Trituration with diethyl ether followed by filtration afforded a first crop of product. The filtrate was purified on silica gel, eluting with dichloromethane to afford the subtitle compound as a colourless solid (combined yield 6.56 g, 73%). Rf 0.31 (ethyl acetate:hexane 20:80, v/v). MS m/z 324 (MNH4)+.

Workup

  1. temperatureThe temperature was maintained between 20° C. and 30° C. for 2 hours
  2. washafter which time the reaction mixture was washed with saturated aqueous sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. filtrationTrituration with diethyl ether followed by filtration
  7. customafforded a first crop of product
  8. customThe filtrate was purified on silica gel
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-16df20eee4f5477c9df9eb6656422042
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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