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4,5-difluoro-2-(trimethylsilyl)phenyl trifluoromethanesulfonate

Cesium Fluoride

phosphite

Acetonitrile

EtOAc

→

Diethyl 3,4-difluorophenylphosphonate

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실험 절차

4,5-difluoro-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (25 mg, 0.078 mmol), Cesium Fluoride (62 mg, 0.411 mmol), Triethtyl phosphite (50 mg, 0.299 mmol), Acetonitrile (1 ml): Reaction Time 4 h; Rf: 0.5 (2:3 EtOAc:Pet Ether); Thick oil; 14.6 mg, 78%; 1H NMR (500 MHz, CDCl3, TMS) δ 7.67-7.55 (m, 2H), 7.31-7.23 (m, 1H), 4.21-4.05 (m, 4H), 1.34 (t, J=7.0 Hz, 6H); 13C NMR (125 MHz, CDCl3, TMS) δ 153.1 (ddd, J=3.8, 12.4, 255.6 Hz), 150.2 (ddd, J=13.4, 22.9, 252.7 Hz), 128.8 (ddd, J=3.8, 6.7, 10.5 Hz), 125.9 (dt, J=3.8, 192.7 Hz), 121.1 (dd, J=11.4, 18.1 Hz), 117.9 (t, J=18.1 Hz), 62.4 (d, J=4.8 Hz), 16.2 (d, J=5.7 Hz) 31P NMR (162 MHz, CDCl3) δ 15.8 (apparent t, JPF=6.1 Hz); HRMS-ESI (m/z) calcd (C10H13F2O3P+H)+: 251.0643. found: 251.0643.

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