Phosphorus tribromide → 3-(4-(2-Bromoethyl)phenyl)-5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazole

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethanol (400 mg, 1.065 mmol) in DCE (20 mL) was added phosphorus tribromide in DCM (1.065 mL, 1.065 mmol). The reaction mixture was heated at 70° C. overnight. The reaction mixture was diluted with dichloromethane and washed with 1N NaOH. The organic layer was dried MgSO4, filtered, and concentrated. The crude material was purified on a 40 gram silica column and eluting with EtOAc/Hex (0-50% gradient over 20 minutes) to afford 77 mg of 3-(4-(2-bromoethyl)phenyl)-5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazole. MS (m+1)=440. HPLC Peak RT=2.40 minutes. (Analytical Method B).

Provenance & Evidence