Triethyl phosphite → Diethyl 2,6-difluorobenzylphosphonate

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2,6-difluorobenzyl bromide (3.0 g, 14.5 mmol) was combined with triethylphosphite (6.2 mL, 36.2 mmol) and the mixture heated and stirred at 135° C. overnight. The mixture was put under hi-vacuum and heated to 80° C. for 10 hours. The final product was a slightly yellow-tinted oil (3.30 g, 86% yield). 1H NMR (400.14 MHz, DMSO) δ 7.36 (m), 7.10 (m, 2H), 3.96 (m, 4H), 3.20 (d, J=21.08 Hz, 2H), 1.16 (t, J=7.05 Hz, 6H). 13C {1H} NMR (100.62 MHz, CDCl3) δ 161.0 (ddd, J=249.0, 7.3, 6.2 Hz, 2C), 128.4 (dt, J=10.2, 3.82 Hz), 111.0 (ddd, J=18.9, 6.0, 3.5 Hz, 2C), 108.5 (dt, J=19.8, 10.5 Hz), 62.1 (d, J=6.5 Hz, 2C), 20.6 (dt, J=142.1, 2.3 Hz), 16.0 (d, J=6.2 Hz, 2C). 31P {1H} NMR (161.97 MHz, DMSO): δ 24.68. Analysis calculated (found) %: C 50.01 (49.71), H 5.72 (5.78). MS (FAB, m/z): 265 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 265.08051 (265.08278).

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