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

HRID 1004034Notes

Reaction equation

HRID 1004034 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-bccc93803f264ed7ab3f513011f3ef46
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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