4-Nitrophenol → 2-((4-Nitrophenoxy)methyl)oxirane

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (1.3 g, 9.6 mmol) was added to a mixture of 4-nitrophenol (1.11 g, 8 mmol) and epibromohydrin (1.37 mL, 16 mmol) The mixture was stirred at 100° C. for 18 hours. After cooling down, the residue was extracted into EtOAc. The organic layer was washed with water, brine and then dried with Na2SO4. Removal of the solvent in vacuo gave an orange residue, which was purified chromatographically on silica eluting with EtOAc/hexanes (1:10, v/v). The product was obtained as a yellow solid (0.8 g, 51%). 1H NMR (300 MHz, CDCl3) δ (ppm): 8.21 (m, 2H), 6.98 (m, 2H), 4.37 (dd, J=2.8 Hz, 11.1 Hz, 1H), 4.00 (dd, J=5.9 Hz, 11.1 Hz, 1H), 3.90 (m, 1H), 2.93 (t, J=4.8 Hz, 1H), 2.77 (dd, J=2.8 Hz, 4.8 Hz, 1H).

Provenance & Evidence