Water → 4-(ALLYLOXY)BENZONITRILE

HRID 734404Notes

Reaction equation

HRID 734404 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH2:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH:11]=[CH2:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 130194-Cyanophenol

Product 1

HCID 2579494-(ALLYLOXY)BENZONITRILE

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Hydroxybenzonitrile (30.0 g, 251.8 mmol), allyl bromide (39.6 g, 327.4 mmol), and cesium carbonate (98.5 g, 302.2 mmol) were dissolved in DMF (900 mL), and 1 mL water was added. After stirring for 12 h at ambient temperature, most of the DMF was removed in vacuo. Water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with H2O and brine. The organic layer was dried over Na2SO4, filtered, and the solvent was removed in vacuo. The title compound was obtained as a white crystalline material (40 g, 100%). 1H NMR (400 MHz, CDCl3) δ 4.60 (d, 2H), 5.34 (d, 1H), 5.43 (d, 1H), 6.03 (m, 1H), 6.96 (d, 2H), 7.58 (d, 2H).

Workup

  1. customwas removed in vacuo
  2. additionWater was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6d9238e3155b49b6a73e40ea1044b37e
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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