Isopropyl iodide → HCID 11457850, compound
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:17]([CH3:19])[CH3:18]>CC(C)=O>[CH:17]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]#[N:2])([CH3:19])[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A reaction mixture of 2-cyanophenol (5 g, 41.55 mmol), cesium carbonate (27.1 g, 83.10 mmol) and 2-iodopropane (7.634 mL, 74.79 mmol) in acetone (80 mL) was heated at 60° C. with vigorous stirring. After 45 min, the gray brown mixture was decanted and the acetone layer was concentrated in vacuo. Water was added to dissolve cesium carbonate, and the product was extracted with diethyl ether (3×200 mL). The organic layers were washed with water, 1 N ammonium hydroxide, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 5% ethyl acetate in hexanes yielded 2-isopropoxy-benzonitrile as a colorless liquid (6.6 g, 99%).
Workup
- customthe gray brown mixture was decanted
- concentrationthe acetone layer was concentrated in vacuo
- additionWater was added
- dissolutionto dissolve cesium carbonate
- extractionthe product was extracted with diethyl ether (3×200 mL)
- washThe organic layers were washed with water, 1 N ammonium hydroxide, brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe solid was then filtered off
- concentrationthe filtrate was concentrated in vacuo
- customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
- washeluting with 5% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-55200c6a746248818e5b17aa41bc3066
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06617346B1
Reaction notes
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