Water → 4-(ALLYLOXY)BENZONITRILE

HRID 2235852Notes

Reaction equation

HRID 2235852 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)BENZONITRILEYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxybenzonitrile (30.0 g, 252 mmol), allyl bromide (39.6 g, 327 mmol), and Cs2CO3 (98.5 g, 302 mmol) were dissolved in DMF (900 mL), and water (1 mL) was added. After stirring for 12 h at rt, the reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with EtOAc (2×). The combined organic layers were washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure yielding 40 g (100%) of the title compound as a white crystalline solid. 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. concentrationthe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a3a6e0a5bf2445cfbbb8f01b8a95a71a
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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