Potassium Carbonate → HCID 70976239, compound

HRID 1484512Notes

Reaction equation

HRID 1484512 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][C:10]([F:13])([F:12])[F:11].Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=2)=[CH:4][C:3]=1[O:9][C:10]([F:11])([F:12])[F:13]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 68322507HCID 68322507, compound2×

Product 1

HCID 70976239HCID 70976239, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-methyl-3-(trifluoromethoxy)phenol (Intermediate 29, 364 mg, 1.89 mmol) and 2 chloro-5-nitropyridine (300 mg, 1.89 mmol) in acetonitrile (4 mL) was added K2CO3 (653 mg, 4.72 mmol) at room temperature. The mixture was heated at reflux for 18 hrs until completion. The resulting mixture was cooled down to room temperature, diluted with water (10 mL) and ethyl acetate (10 mL). Phases were separated, the organic layer was washed with an aqueous 10% solution of ammonium chloride (10 mL) and aqueous 13% solution of NaCl (10 mL). The organic layer was dried over Na2SO4 and evaporated to dryness to give the title compound (594 mg) as pale brown oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hrs until completion
  3. customPhases were separated
  4. washthe organic layer was washed with an aqueous 10% solution of ammonium chloride (10 mL) and aqueous 13% solution of NaCl (10 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1a9f0f1bc4ca4eefa5bb0422b6ac8e01
Source dataset
uspto-grants-2016_08
Patent number
US09422252B2

Reaction notes

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