Iodine chloride → 2-(3-Ethoxy-4-iodo-phenyl)-2-methyl-propionitrile
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]([CH3:14])([CH3:13])[C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)[CH3:2].[I:15]Cl>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]([CH3:13])([CH3:14])[C:11]#[N:12])[CH:7]=[CH:8][C:9]=1[I:15])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(3-Ethoxy-phenyl)-2-methyl-propionitrile (2.96 grams, 15.65 mmol) was dissolved in a freshly prepared acetic acid solution of iodine monochloride (20 mL of a 1.54 M iodine monochloride solution in acetic acid, 30.8 mmol). The reaction was slightly exothermic. The reaction mixture was allowed to stand at room temperature for 3 d. The reaction mixture was concentrated, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 10% sodium carbonate (1×), brine (1×), and dried (anhydrous magnesium sulfate). The solids were filtered off, and the filtrate was concentrated to dryness. The residue was purified by flash chromatography 110 g of silica gel, eluting with a gradient of ethyl acetate in hexanes) to give 2-(3-ethoxy-4-iodo-phenyl)-2-methyl-propionitrile (2.53 g, 51%). LR-MS: 316.21 [(M+H)+]