Triphenylphosphine → (2-(Benzyloxy)-3,5-difluorophenethyl)triphenylphosphonium, iodide salt

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(benzyloxy)-1,5-difluoro-3-(2-iodoethyl)benzene (630 mg, 1.684 mmol) in toluene (8 ml) was added Ph3P (442 mg, 1.684 mmol) and the mixture was heated at 100° C. for 16 h. The mixture was then cooled to rt and toluene was decanted via pipet and remaining residue was washed with ether and ethyl acetate, dried under high vac to afford (2-(benzyloxy)-3,5-difluorophenethyl)triphenylphosphonium, iodide salt (600 mg, 0.943 mmol, 56.0% yield) as white solid. Used as-is in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.81-7.71 (m, 9H), 7.62 (td, J=7.8, 3.5 Hz, 5H), 7.39-7.33 (m, 2H), 7.31 (d, J=7.6 Hz, 1H), 7.25 (d, J=7.3 Hz, 2H), 7.22-7.14 (m, 2H), 6.75 (ddd, J=11.2, 8.2, 2.8 Hz, 1H), 5.01 (s, 2H), 3.92 (dt, J=12.4, 7.9 Hz, 2H), 3.02-2.94 (m, 2H).

Provenance & Evidence