Isopropyl iodide → 3-(Propan-2-yloxy)benzonitrile

HRID 1510111Notes

Reaction equation

HRID 1510111 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].I[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+]>CC#N.C(Cl)Cl>[CH:11]([O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 133943-Cyanophenol

Product 1

HCID 223440163-(Propan-2-yloxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A combination of 32 g (268 mmol, Aldrich) 3-cyanophenol, 26.9 mL (268 mmol) 2-iodopropane, and 88 g (269 mmol) cesium carbonate in 1:1 CH2Cl2:CH3CN was heated to reflux and allowed to stir overnight. HPLC/MS showed pure product so the suspension was filtered, washed with CH3CN and concentrated. The remaining oil was dissolved in CH2Cl2 and filtered thru a short pad of silica with CH2Cl2. The filtrate was concentrated to dryness to give the product. An alternative preparation uses the conditions similar to the above except that potassium carbonate is used as the base.

Workup

  1. temperatureto reflux
  2. filtrationwas filtered
  3. washwashed with CH3CN
  4. concentrationconcentrated
  5. dissolutionThe remaining oil was dissolved in CH2Cl2
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to dryness
  8. customto give the product
  9. customAn alternative preparation

Sources & evidence

ORD record
ord-62654e9d211942e99a83c7f5ffb71e8b
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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