Triethyl Phosphate → Diethyl (2-bromo-1-oxoindan-4-yl)methylphosphonate

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Reaction Steps

The diethyl 1-oxoindan-4-ylmethylphosphonate can be prepared in the following manner: a mixture of 0.5 g of 4-(bromomethyl)indan-1-one, 0.9 g of triethyl phosphate and 5 ml of xylene is heated at reflux for 5 hours. The reaction medium is concentrated in a rotary evaporator and then the residue is purified by chromatography on silica, eluting with an ethyl acetate-petroleum ether (85-15 by volume) mixture. 0.4 g of diethyl (2-bromo-1-oxoindan-4-yl)methylphosphonate is obtained in the form of a colourless oil [1H NMR spectrum in DMSO-d6, T=300K, δ in ppm (250 MHz): 1.20 (6H, t, J=6 Hz, 2 CH3), 2.70 (2H, m, CH2CO), 3.20 (2H, m, CH2), 3.38 (2H, d, J=22 Hz, PCH2), 4.00 (2H, q, J=6 Hz, OCH2), 7.45 (1H, t, J=7 Hz, arom. CH), 7.60 (2H, m, 2 arom. CH)].

Provenance & Evidence