Water → HCID 47002646, compound

HRID 1506142Notes

Reaction equation

HRID 1506142 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[N+:21]([CH3:24])([O-])=O>[Zn]>[NH2:21][CH2:24][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([OH:13])[C:9]([F:11])([F:12])[F:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 11430Potassium CarbonateHCID 67578Ethanone, 1-(4-chlorophenyl)-2,2,2-trifluoro-

Product 1

HCID 47002646HCID 47002646, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

1-(4-Chlorophenyl)-2,2,2-trifluoroethanone (2.00 g, 9.59 mmol) in nitromethane (10 mL) was stirred with potassium carbonate (1.32 g, 9.59 mmol) at room temperature for 1 hour. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue (pale yellow amorphous, 3.3 g) was dissolved in ethanol (52 mL), then 6 M hydrochloric acid was added dropwise under cooling with ice, and zinc powder (3.13 g, 48.0 mmol) was gradually added. The reaction mixture was stirred for one day while the temperature was gradually raised to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was mixed with 28 wt % aqueous ammonia and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1 (v/v)) to give the title compound as a colorless solid (609 mg, yield 26%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue (pale yellow amorphous, 3.3 g) was dissolved in ethanol (52 mL)
  5. addition6 M hydrochloric acid was added dropwise
  6. additionwas gradually added
  7. filtrationfiltered through Celite
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. additionThe residue was mixed with 28 wt % aqueous ammonia
  10. extractionextracted with chloroform
  11. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1 (v/v))

Sources & evidence

ORD record
ord-c5acd76c47fe400f93281c57880de60c
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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