Triethyl phosphite → HCID 86603456, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3,5-dichloro-4-[3′-(4-fluorobenzyl)-4-hydroxyphenoxy] benzyl bromide (0.25 g, 0.55 mmol) in toluene (5 mL) at room temperature was added triethylphosphite (0.91 g, 5.5 mmol). The reaction mixture was heated at 120° C. for 8 h and cooled to room temperature. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:1) to afford diethyl 3,5-dichloro-4-[3′-(4-fluorobenzyl)-4′-hydroxyphenoxy]benzylphosphonate as a colorless oil (0.2 g, 68%): 1H NMR (300 MHz, CDCl3): δ 7.29 (d, J=2.7 Hz, 2H), 7.15 (dd, J=5.4, 9.0 Hz, 2H), 6.95 (t, J=8.7 Hz, 2H), 6.66 (d, J=4.8 Hz, 1H), 6.65 (s, 1H), 6.46 (dd, J=3.0, 8.7 Hz, 1H), 4.07 (q, J=7.2 Hz, 4H), 3.89 (s, 2H), 3.04 (d, J=21.3 Hz, 2H), 1.27 (t, J=7.2 Hz, 3H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:1); Rf=0.3.

Provenance & Evidence