3-Cyanophenol → HCID 15421717, compound

HRID 1919807Notes

Reaction equation

HRID 1919807 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH:10]1(Br)[CH2:12][CH2:11]1.N12CCCN=C1CCCCC2>O>[CH:10]1([O:9][C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 133943-CyanophenolHCID 78037BromocyclopropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 15421717HCID 15421717, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Irradiate (200 C, ˜6 W [150 W max.], ˜25 psi) a solution of 3-cyanophenol (9.5 g, 80 mmol), cyclopropyl bromide (8.0 mL; 100 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (18 mL, 120 mmol) divided equally into five 10-mL tubes for 15 min. with stirring and cooling. After cooling, take the dark reaction mixtures together in water (200 mL) and extracted with ether (200 mL). Wash the organic layer with 0.2 M aq NaOH (40 mL, salted), 0.2 M aq HCl (100 mL, salted), and water (100 mL, salted). Dry the organic layer (Na2SO4) and rotary evaporate (30° C.) yielding 3-cyclopropoxybenzonitrile (4.56 g, 28.65 mmol, 36% yield) as a dark brown liquid. GCMS: 4.20 min.; EIMS m/z 159.

Workup

  1. temperaturecooling
  2. temperatureAfter cooling
  3. extractionextracted with ether (200 mL)
  4. washWash the organic layer with 0.2 M aq NaOH (40 mL, salted), 0.2 M aq HCl (100 mL, salted), and water (100 mL, salted)
  5. dry with materialDry the organic layer (Na2SO4)
  6. customrotary evaporate (30° C.)

Sources & evidence

ORD record
ord-62d02325bfc349e39d7fcf4838a23928
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

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