Benzyl Bromide → Benzoic acid 4-benzyloxy-3-nitro-phenyl ester

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Reaction Steps

A mixture of benzoic acid 4-hydroxy-3-nitro-phenyl ester (Tapia, R.; Torres, G. and Valderrama, J. A. Synth. Commun. 1986, 16, 681) (20.7 g, 80 mmol), benzyl bromide (42.75 g, 250 mmol), potassium carbonate (48.3 g, 350 mmol) and DMF (300 mL) was stirred at room temperature for 2 days. After removing the solvent the residue was dissolved in water and extracted with CH2Cl2. The organic extracts were dried (MgSO4) and concentrated. The product was purified by flash silica gel chromatography eluting with CH2Cl2 to give the title compound as a pale yellowish solid (25.1 g, 90%); 1H NMR (300 MHz, CDCl3) δ 5.27(s, 2H), 7.17 (d, J=9.1 Hz, 1H), 7.30-7.55 (m, 8H), 7.60-7.70 (m, 1H), 7.80 (d, J=2.9 Hz, 1H), 8.15-8.25 (m, 2H); MS (ES) m/z: 345.0 (MH+, 100%); HRMS Calcd. for C20H15NO5 (M+): 349.0951. Found: 349.0952.

Provenance & Evidence