1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Azidomethyl-2-iodo-benzene

Participants

Reaction Steps

To a solution of 2-iodobenzyl alcohol (6.0 g, 25.4 mmol) and DPPA (6.8 mL, 30.5 mmol) in toluene (65 mL) was added DBU (5.0 mL, 33.0 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then diluted with 3M HCl (60 mL) and ether (150 mL). The organic phase was separated and the aqueous phase was extracted with ether (×3). The combined organic extracts were washed with water (×2) and and then with brine. The solution was dried over anhydrous Na2SO4 and concentrated in vacuo. Silica gel column chromatography using 95:5 hexanes:EtOAc afforded 6.1 g (93%) of 1-azidomethyl-2-iodo-benzene.

Provenance & Evidence