Potassium Carbonate → HCID 58046318, compound

HRID 2359321Notes

Reaction equation

HRID 2359321 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[OH:14].[F:15][C:16]1[CH:23]=[C:22](F)[C:21]([F:25])=[CH:20][C:17]=1[C:18]#[N:19].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:15][C:16]1[CH:23]=[C:22]([O:14][C:4]2[CH:5]=[CH:6][C:7]([O:9][C:10]([F:12])([F:11])[F:13])=[CH:8][C:3]=2[O:2][CH3:1])[C:21]([F:25])=[CH:20][C:17]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5938132,4,5-TrifluorobenzonitrileHCID 58046344HCID 58046344, compound

Product 1

HCID 58046318HCID 58046318, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-methoxy-4-(trifluoromethoxy)phenol (Preparation 54, 331 mg, 1.59 mmol) in dimethylsulfoxide (10 mL) was added 2,4,5-trifluorobenzonitrile (250 mg, 1.59 mmol) and potassium carbonate (220 mg, 1.59 mmol) This suspension was stirred for 18 hours at room temperature. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (20 mL), and extracted with dichloromethane (3×40 mL). The combined organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound as a clear oil (549 mg, 100%). This was used in the next reaction with no further purification.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution (20 mL)
  2. extractionextracted with dichloromethane (3×40 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a8e131e0523c4658812be666b10030c4
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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