Triethyl phosphite → 2-(Diethoxyphosphorylmethyl)-5-nitro-benzenesulfonic Acid, 2,2-Dimethylpropyl Ester

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Reaction Steps

2-Bromomethyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl ester (Example 44, 2.0 g, 5.46 mmol) was dissolved in 100 mnL of anhydrous o-xylene. To this solution was added triethylphosphite (3.75 mL, 21.84 mmol). A water cooled condenser was attached and the material was heated to exactly 100° C. After six hours the mixture was cooled to room temperature then diluted with with ethyl acetate (400 mL) and washed with brine (2×). After drying over MgSO4 the organic layer was concentrated on a rotovap and then purified by flash column chromatography using 50 to 60% ethyl acetate/hexanes gradient as an eluant to provide 1.34 g of the title compound as a yellow oil.(55%): 1HNMR (CDCl3) δ8.87 (m, 1H), 8.43 (dd, J=9 Hz, 2 Hz, 1H), 8.05 (dd, J=9 Hz, 2 Hz, 1H), 4.12 (m, 4H), 3.81 (s, 2H), 3.77 (d, J=23 Hz, 2H), 1.32 (m, 6H), 0.96 (s, 9H); MS (ES-POS): [M+Na]+ 446; Analytical HPLC determined that this compound was 96.1% pure by C-18 reverse phase.

Provenance & Evidence