Water → HCID 66330671, compound

HRID 230799Notes

Reaction equation

HRID 230799 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([O:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:18]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7456Methylparaben2×HCID 11430Potassium CarbonateHCID 1449582-Chloro-4-(trifluoromethyl)pyridine

Product 1

HCID 66330671HCID 66330671, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-4-trifluoromethylpyridine (1.0 g), methyl 4-hydroxybenzenecarboxylate (838.3 mg) and potassium carbonate (2.28 g) were suspended in acetonitrile (10 mL), heated under reflux for 27 hours, and methyl 4-hydroxybenzenecarboxylate (838.3 mg) was added thereto and further heated under reflux for 24 hours. Water (100 mL) was added to the reaction liquid, extracted with ethyl acetate (100 mL), and the organic layer was washed with aqueous 2 N sodium hydroxide solution (100 mL), water (100 mL) and saturated saline water (100 mL) in that order, dried with magnesium sulfate, and evaporated under reduced pressure to obtain a pale yellow oil. The resulting oil was purified through silica gel column chromatography (hexane/ethyl acetate=8/2) to obtain the entitled compound (740 mg) as a colorless solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 27 hours
  3. temperaturefurther heated
  4. temperatureunder reflux for 24 hours
  5. extractionextracted with ethyl acetate (100 mL)
  6. washthe organic layer was washed with aqueous 2 N sodium hydroxide solution (100 mL), water (100 mL) and saturated saline water (100 mL) in that order
  7. dry with materialdried with magnesium sulfate
  8. customevaporated under reduced pressure
  9. customto obtain a pale yellow oil
  10. customThe resulting oil was purified through silica gel column chromatography (hexane/ethyl acetate=8/2)

Sources & evidence

ORD record
ord-66ec96960cb641f9b31240a569a0eb26
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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