Acetone Cyanohydrin → 2-(4-Chloro-2-iodophenyl)acetonitrile

Participants

Reaction Steps

(4-Chloro-2-iodophenyl)methanol (4.67 g, 17 mmol) and PPh3 (6 mL, 26 mmol) were stirred in Et2O at 0° C. Diisopropyl azodicarboxylate (5 mL, 26 mmol) was added dropwise, and the reaction was stirred for 20 minutes (a white precipitate formed). A solution of acetone cyanohydrin (2 mL, 26 mmol) in diethyl ether (5 mL) was added dropwise to the reaction. The resulting solution was stirred for 5 minutes at 0° C. and then allowed to warm to room temperature over two hours. The reaction was monitored by TLC and LCMS. The mixture was filtered, and the filtrate was concentrated in vacuo. Purification was done using silica flash chromatography with a gradient of 0-15% EtOAc/hexanes. MS m/e=278 (M+H)+.

Provenance & Evidence