Ammonia → 2-Phenoxymethyl-benzofuran-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a 1-methyl-2-pyrrolidinone (10 mL) solution of 5-iodo-2-phenoxymethyl-benzofuran (250 mg, 0.714 mmol) described in Production Example 75-1-1 were added zinc cyanide (168 mg, 1.43 mmol) and tetraquis(triphenylphosphine) palladium (0) (165 mg, 0.143 mmol). This mixture was stirred at 130° C. for 3 hours. After adding ice water and concentrated aqueous ammonia to the reaction mixture and stirring, the reaction mixture was extracted with ethyl acetate. The organic layer was separated followed by washing with sat. NaCl, drying over anhydrous magnesium sulfate and concentrating under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (27 mg, 15%).

Provenance & Evidence