Hydrochloric Acid → (2-Fluoro-6-iodophenyl)methanamine

Participants

Reaction Steps

Under an argon atmosphere, 123 mg of 2-fluoro-6-iodobenzonitrile was dissolved in 2 mL of tetrahydrofuran, and 1.5 mL of a borane/tetrahydrofuran complex was added thereto, followed by stirring under reflux overnight. The reaction liquid was cooled to room temperature, and 2N hydrochloric acid was added thereto, followed by further stirring for 1 hour. After completion of the reaction, to the reaction liquid was added an aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate, and the organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 87 mg (70%) of 2-fluoro-6-iodobenzylamine as a light yellow oily substance. This product, 68 mg of di-tert-butyl dicarbonate, and 31 mg of triethylamine were dissolved in 1 mL of chloroform, followed by stirring at room temperature for 1 hour. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (n-hexane:ethyl acetate=2:1) to obtain 80 mg (yield 81%) of a title compound as a light yellow solid.

Provenance & Evidence