Potassium Carbonate → 3,4-Dimethoxy-2-(2,2,2,-trifluoroethoxy)benzonitrile

HRID 2228521Notes

Reaction equation

HRID 2228521 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].O([CH2:28][C:29]([F:32])([F:31])[F:30])S(C(F)(F)F)(=O)=O>CN(C)C=O.ClCCl>[CH3:17][O:16][C:15]1[C:8]([O:7][CH2:28][C:29]([F:32])([F:31])[F:30])=[C:9]([CH:12]=[CH:13][C:14]=1[O:18][CH3:19])[C:10]#[N:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 119947582-Hydroxy-3,4-dimethoxybenzonitrile

Product 1

HCID 184706363,4-Dimethoxy-2-(2,2,2,-trifluoroethoxy)benzonitrileYield 94.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Potassium carbonate (6.91 g, 0.05 mol) was added to a stirred solution of 2-hydroxy-3,4-dimethoxybenzonitrile (from Example 10(c), 5.61 g, 0.031 mol) in dimethylformamide (30 ml). This was followed by the addition of a solution of 2,2,2-trifluoroethyl triflate (23.2 g, 0.10 mol). in dichloromethane (100 ml ) and the reaction was stirred at room temperature for 18 hours. The reaction was partitioned between 2N hydrochloric acid and ethyl acetate, the organic layer separated, washed sequentially with saturated aqueous brine and water, dried (MgSO4) and evaporated under reduced pressure. Trituration with diethyl ether followed by filtration afforded the subtitle compound as a colourless solid (7.67 g, 94%). Rf 0.76 (dichloromethane:methanol 95:5, v/v). MS m/z 279 (MNH4)+.

Workup

  1. customThe reaction was partitioned between 2N hydrochloric acid and ethyl acetate
  2. customthe organic layer separated
  3. washwashed sequentially with saturated aqueous brine and water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. filtrationTrituration with diethyl ether followed by filtration

Sources & evidence

ORD record
ord-2168aaa6dd7c4f8ba59e5f6102d981fe
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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