N,N-Dimethylglycine → [2-Nitro-4-(3-nitro-phenoxy)-phenyl]-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a sealed tube are charged with 3-nitrophenol (83 mg, 0.6 mmol), (4-bromo-2-nitro-phenyl)-acetic acid ethyl ester (180 mg, 0.63 mmol), copper iodide (12 mg, 0.06 mmol), N,N-dimethylglycine (23 mg, 0.2 mmol), Cs2CO3 (400 mg, 1.2 mmol) in 1,4-dioxane. The resulting mixture is stirred at 120° C. for 24 h. The reaction mixture is diluted with water and extracted with EtOAc. The organic phase is dried, concentrated, and purified by flash column chromatography (DCM/Hexane=9:1) to give 130 mg of the desired product (yield 62%). 1H NMR (400 MHz, CDCl3) δ 8.00-7.97 (m, 1 H), 7.82-7.81 (m, 1 H), 7.70-7.69 (m, 1 H), 7.53-7.49 (m, 1 H), 7.34-7.30 (m, 1 H), 7.22-7.19 (m, 1 H), 4.14-4.09 (m, 2 H), 3.94 (s, 2 H), 1.23-1.18 (m, 3 H). LC/MS: 347.2 (MH+).

Provenance & Evidence