1,2-Dichloroethane → Methyl 4-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a suspension of mono-methyl terephthalate (1.50 g, 8.33 mmol) in acetonitrile (16 mL) was added EDC (4.65 g, 25.0 mmol), HOBt (1.12 g, 8.33 mmol), DIPEA (3.24 g, 25.0 mmol) and N-hydroxybenzimidamide (1.36 g, 10.0 mmol). The reaction was heated at 100° C. for 30 mins in a microwave. The reaction was then cooled to rt, diluted with water (60 mL) and isolated the crude white precipitate by vacuum filtration. Dissolved in CH2Cl2 and passed through a plug of silica to afford methyl 4-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoate as an off-white solid (640 mg, 23%). 1H-nmr (400 MHz, CDCl3) δ 8.33 (d, J=8 Hz, 2H), 8.24 (d, J=8 Hz, 2H), 8.21-8.11 (m, 2H), 7.59-7.51 (m, 3H), 4.00 (s, 3H); MS (ESI) m/z 280.9

Provenance & Evidence