Water → 2-(Benzyloxy)-4-fluoro-1-nitrobenzene

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Reaction Steps

To a suspension of K2CO3 (2.07 g, 15 mmol) in DMF (8 mL) is added 5-fluoro-2-nitrophenol (1.57 g, 10 mmol), followed by benzyl bromide (1.75 g, 10.2 mmol). The mixture is stirred at ambient temperature for 18 h, then poured into water and extracted into EtOAc. The organic phase is washed with water (3×), saturated NaCl (1×) and dried over sodium sulfate. The solvent is removed under reduced pressure and the residual oil filtered through a pad of silica gel using DCM to elute 2-benzyloxy-4-fluoro-1-nitrobenzene as a yellow oil, which slowly solidifies on standing: mp=52-54° C.; 1H NMR (CDCl3) δ 8.03-7.98 (m, 2H), 7.53-7.36 (m, 5H), 6.66 (dd, J=10.17, 2.64 Hz, 1H), 6.81-6.73 (m, 1H), 5.26 (s, 2H).

Provenance & Evidence