Water → 4-(ALLYLOXY)BENZONITRILE

HRID 1629718Notes

Reaction equation

HRID 1629718 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 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzonitrile (20.7 g, 169 mmol) and allyl bromide (27.1 g, 220 mmol) in DMF (620 mL) was added Cs2CO3 (66.7 g, 203 mmol) and water (0.67 mL). The resulting mixture was stirred at room temperature overnight and concentrated. The residue was partitioned between water and EtOAc and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give INT 24 which was used in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between water and EtOAc
  3. extractionthe aqueous layer was further extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give INT 24 which
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-2ab18214185f4667b7b9595d7b671bf3
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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