4-Methoxybenzyl alcohol → HCID 24777661, compound

HRID 2063585Notes

Reaction equation

HRID 2063585 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22](F)[C:19]=1[C:20]#[N:21]>CN(C)C=O>[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:19]=1[C:20]#[N:21]

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 10796Cesium carbonateHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 24777661HCID 24777661, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methoxybenzyl alcohol (5.0 g) and cesium carbonate (8.3 g) were added to an N,N-dimethylformamide (0.5 L) solution of 2,6-difluorobenzonitrile (7.0 g), and stirred for 15 hours. 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 (6.6 g).

Workup

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

Sources & evidence

ORD record
ord-6e599472894d43bcad18b5cb1d5efa46
Source dataset
uspto-grants-2012_10
Patent number
US08288396B2

Reaction notes

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