4-Benzyl 1-Methyl 2-nitroterephthalate synthesis

Yield:402925-14-8 63%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide;

Steps:

72.B benzyl 3-nitro-4-methoxycarbonylbenzoate

Example 72B benzyl 3-nitro-4-methoxycarbonylbenzoate To a solution of methyl 2-nitro-4-carboxybenzoate (1.13 g, 5.00 mmol), K₂CO₃ (680 mg, 4.92 mmol) in N,N-dimethylformamide (5 mL) was added benzyl bromide (750 μL, 6.30 mmol). The mixture was heated at 100° C. for 15 minutes, cooled to ambient temperature, poured into water (30 mL) and extracted with diethyl ether (3*10 mL). The combined ether layers were washed with water (2*10 mL), brine (1*10 mL), dried (MgSO₄), filtered, and concentrated under reduced pressure. The residue was crystallized from 20% ethyl acetate/hexanes to provide the titled compound (1.0 g, 63%). ¹H NMR (300 MHz, d₆-DMSO) δ8.52 (d, 1, J=1.7), 8.39 (dd, 1, J=1.7, 8.1), 8.01 (d, 1, J=7.8), 7.53-7.35 (m, 5), 5.43(s,2), 3.89 (s,3); MS (ESI) m/z=333 (M+NH₄⁺).

References:

US2002/35137,2002,A1