Triethyl phosphite → Diethyl (4-Bromobenzyl)phosphonate

Participants

Reaction Conditions

Reaction Steps

1-bromo-4-(bromomethyl)benzene (5.0 g, 20 mmol) and triethyl phosphite (51 mL, 300 mmol) were mixed in a round bottom flask and refluxed at 90° C. for 19 hours. Excess triethyl phosphite was removed under reduced pressure and the product purified by flash chromatography (1:1 Hexane/EtOAc) to give compound 16. 16: 98% yield; colorless liquid; 1H NMR (400 MHz, CDCl3) δ 7.30 (d, 2H, J=7.5 Hz), 7.05 (d, 2H, J=7.6 Hz), 3.99-3.88 (m, 4H), 2.99 (s, 1H), 2.94 (s, 1H), 1.12 (t, 6H, J=106.9 Hz); 13C NMR (100 MHz, CDCl3) δ 131.7, 131.6, 131.5, 121.0, 62.3, 34.0, 32.0, 16.5; HRMS Calc for C11H16BrO3P (M+H)+ 307.0097 found 307.0093.

Provenance & Evidence