Benzyl Bromide → Methyl 3-(benzyloxy)-4-nitrobenzoate

Beteiligte Stoffe

Reaktionsschritte

REFERENCE: J. Med Chem. 1997, 40, 105-111. To an acetone solution (500 mL) of methyl 3-hydroxy-4-nitrobenzoate (25.0 g, 126.8 mmol) was added cesium carbonate (61.9 g, 190.2 mmol) followed by benzyl bromide (15.0 mL, 126.8 mmol). The reaction was heated to reflux and monitored by TLC. The reaction was judged complete in approximately 7 h. The reaction was then cooled to room temperature and concentrated under reduced pressure to approximately 20 mL. The residue was diluted with ethyl acetate (700 mL) and washed in succession with 1N hydrochloric acid, 1N sodium hydroxide, 1N hydrochloric acid and finally with saturated aqueous sodium chloride. The organic layer was then dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield 3-benzyloxy-4-nitro-benzoic acid methyl ester as a solid. 1H NMR (CDCl3) 7.83(m,2H), 7.70(dd, 1H), 7.50-7.30(m,5H), 5.28(s,2H), 3.96(s,3H).

Herkunft & Nachweise