Potassium Carbonate → HCID 66617415, compound

HRID 2063584Notes

Reaction equation

HRID 2063584 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:19]=1[C:20]#[N:21]>CC(C)=O>[F:17][C:18]1[CH:25]=[C:24]([O:26][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:23]=[CH:22][C:19]=1[C:20]#[N:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 66617415HCID 66617415, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Methoxybenzyl chloride (5.0 g) and potassium carbonate (8.3 g) were added to an acetone (0.5 L) solution of 2-fluoro-4-hydroxybenzonitrile (4.1 g), and stirred with heating under reflux for 15 hours. After cooled to room temperature, the reaction solution was evaporated under reduced pressure, water (50 mL) was added to the residue, extracted with ethyl acetate, dried with sodium sulfate and concentrated under reduced pressure. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a white solid (7.2 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 15 hours
  3. customthe reaction solution was evaporated under reduced pressure, water (50 mL)
  4. additionwas added to the residue
  5. extractionextracted with ethyl acetate
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-912f1d636e3c47bf80edc9909e76a9cc
Source dataset
uspto-grants-2012_10
Patent number
US08288396B2

Reaction notes

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