Isopropyl iodide → HCID 11457850, compound

Temperature

60 °C

A mixture of 2-cyanophenol (5.0 g, 42 mmol), cesium carbonate (27.1 g, 82.9 mmol) and 2-iodopropane (7.63 mL, 76 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 the solid, and the mixture was extracted with diethyl ether (3×200 mL). The organic layers were washed with water, 1 N ammonium hydroxide and brine, and dried over anhydrous sodium sulfate. The solids were 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 (6.6 g, 97%) as a colorless liquid.

1. customthe gray brown mixture was decanted
2. concentrationthe acetone layer was concentrated in vacuo
3. additionWater was added
4. dissolutionto dissolve the solid
5. extractionthe mixture was extracted with diethyl ether (3×200 mL)
6. washThe organic layers were washed with water, 1 N ammonium hydroxide and brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationThe solids were then filtered off
9. concentrationthe filtrate was concentrated in vacuo
10. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
11. washeluting with 5% ethyl acetate in hexanes

ORD record

ord-86bf620f8dc242f3b43991fab3063646

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06734302B2