Isopropanol → 5-Bromo-2-chloro-3-(4-isopropoxybenzyl)thiophene

Participants

Reaction Steps

To a solution of phenol 4 (1 g, 3.29 mmol) and PPh3 (1.8 g, 6.58 mmol) in THF (25 mL) was added DIAD (1.3 mL, 6.58 mmol) at room temperature. The mixture was stirred at room temperature for 30 min. 2-Propanol (0.4 mL, 4.94 mmol) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 20 hours. The mixture was extracted with EtOAc/H2O (50 mL/50 mL) and was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the desired product 6 (913 mg, 80%).

Provenance & Evidence