Triphenylphosphine → HCID 11722548, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-fluorophenol (0.612 g, 3.2 mmol; described: in Finger et al. J. Amer. Chem. Soc. 1959, 81, 94), 4-(2-hydroxyethyl)morpholine (0.47 ml, 3.84 mmol) and triphenylphosphine (1.0 g, 3.84 mmol) was dissolved in anhydrous tetrahydrofuran (5 mL) and cooled to 0° C. Diethyl azodicarboxylate (0.6 mL, 3.84 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 3.5 h. The solvent was evaporated and the residue partioned between water and methylene chloride. The organic phase was washed twice with a saturated sodium hydrogen carbonate solution, dried (MgSO4) and the solvent was evaporated. The product was purified by column chromatography on silica using a gradient of toluene/acetonitrile, (4:1 to 0:1), as the eluent to give 0.655 g (67% yield) of the title compound as a clear oil: 1H NMR (CDCl3) δ 7.21 (d, J=11 Hz, 1H), 7.16 (m, 1H), 6.83 (t, J=9 Hz, 1H), 4.14 (t, J=6 Hz, 3H), 3.71 (t, J=5 Hz, 4H), 2.80 (t, J=6 Hz, 2H), (t, J=5 Hz, 4H); 13C NMR (CDCl3, 100) δ 154.2, 151.7, 146.5, 146.4, 127.4, 127.4, 120.1, 119.9, 116.8, 116.8, 112.7, 112.7, 68.1, 67.1, 57.6, 54.3; MS (ESP) m/z 304, 306 (M++1).

Provenance & Evidence