Ethyl Acetate → 849811-45-6

HRID 2080047Notes

Reaction equation

HRID 2080047 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.F[C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14].CC(C)([O-])C.[K+].C(OCC)(=O)C>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 97433-FluorophenolHCID 678803-FluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 23130454849811-45-6Yield 33%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 3-fluoro-phenol (500 mg, 4.46 mmol) and 3-fluoro-benzonitrile (540 mg, 4.46 mmol) in dimethylsulfoxide (1.0 mL) was added potassium tert-butoxide (500 mg, 4.46 mmol), and the solution was stirred at 140° C. for 3 hours. The reaction solution was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1), and 3-(3-fluoro-phenoxy)-benzonitrile (313 mg, 33%) was obtained as a yellow solid.

Workup

  1. customwas allowed to room temperature
  2. customfor partitioning
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-0f88ded8aba5416caada27548645fcf2
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…