Potassium Carbonate → HCID 86624792, compound

Participants

Reaction Conditions

Reaction Steps

4-Fluoro-2-nitrophenol (13.5 g, 86 mmol) was dissolved in anhydrous DMF (100 mL) under an N2 atmosphere and treated sequentially with K2CO3 (23.7 g, 172 mmol) and trans-cinnamyl chloride (13.4 g, 87.6 mmol) and heated to 60° C. for 12 h. Upon completion, the reaction was diluted with EtOAc (500 mL), and washed with H2O (3×300 mL) and sat. aq. NaCl (500 mL). The organic layer was dried with MgSO4, filtered and concentrated to yield a yellow solid which was easily recrystallized from EtOAc/hexanes to provide pure 4-fluoro-2-nitrophenyl (2E)-3-phenylprop-2-enyl ether (5-1). 1H NMR (300 MHz, CDCl3) δ 7.61 (dd, J=7.5, 2.5 Hz, 1H), 7.41 (app d, J=7.0 Hz, 2H), 7.34 (t, J=7.5 Hz, 2H), 7.27 (m, 2H), 7.12 (dd, J=9.0, 4.0 Hz, 1H), 6.76 (d, J=16.0 Hz, 1H), 6.37 (dt, J=16.0, 5.5 Hz, 1H), 4.83 (dd, J=5.5, 1.0 Hz, 2H).

Provenance & Evidence