Benzyl Alcohol → HCID 18452899, compound

HRID 1271508Notes

Reaction equation

HRID 1271508 reaction equation
[F:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:18]([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:18]([O:25][C:8]1[CH:9]=[C:2]([F:1])[C:3]([C:4]#[N:5])=[C:6]([F:11])[CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 7371772,4,6-Trifluorobenzonitrile

Product 1

HCID 18452899HCID 18452899, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 2,4,6-trifluorobenzonitrile (314 mg, 2.00 mmol) and potassium carbonate (828 mg, 6.00 mmol) in dry N,N-dimethylformamide (3 mL) at 100° C. was added a solution of benzyl alcohol (216 mg, 2.00 mL) in dry N,N-dimethylformamide (1 mL) using a syringe pump over 4 h and the resulting mixture was stirred at 100° C. for 1 h. The reaction mixture was stirred at room temperature overnight and water and ethyl acetate were added and the phases separated. The organic phase was washed with 1.2 M hydrochloric acid (3×) and the combined organic phases were back-extractted with ethyl acetate (3×). The organic phases were dried (sodium sulfate), filtered, concentrated in vacuo and the residue was purified by flash chromatography (silica gel, hexanes-ethyl acetate 15:1) to give a white solid, mixture of regioisomers. The title product was obtained as a white solid (51 mg, 10%) by HPLC purification (reversed phase).

Workup

  1. customover 4 h
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. customthe phases separated
  4. washThe organic phase was washed with 1.2 M hydrochloric acid (3×)
  5. dry with materialThe organic phases were dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by flash chromatography (silica gel, hexanes-ethyl acetate 15:1)
  9. customto give
  10. additiona white solid, mixture of regioisomers

Sources & evidence

ORD record
ord-7de380e0f2f54e598a3d7066f74d4a44
Source dataset
uspto-grants-2007_04
Patent number
US07205313B2

Reaction notes

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