Benzyl Bromide → HCID 18433467, compound

Participants

Reaction Steps

To a mixture of (7-hydroxy-naphthalen-1-yl)-carbamic acid tert-butyl ester (5.11 g, 19.7 mmol) and potassium carbonate (3.26 g, 23.6 mmol) in N,N-dimethylformamide is added benzyl bromide (3 mL, 4.31 g, 25.2 mmol) slowly. The mixture is then stirred at room temperature over night and poured into ice-water (150 mL). The resulting mixture is extracted with ethyl acetate (4×100 mL) and the organic portions are combined, washed with water and brine, dried over sodium sulfate, concentrated and purified by silica gel chromatography (Hexanes/EtOAc=15/1) to give (7-benzyloxy-naphthalen-1-yl)-carbamic acid tert-butyl ester (5.93 g, 86.3%); 1H NMR 400 Hz (CDCl3) δ1.60 (s, 9H), 5.22 (s, 2H), 6.63 (br, 1H), 7.27 (m, 2H), 7.38 (m, 2H), 7.45 (m, 2H), 7.44 (d, J=7.44 Hz, 2H), 7.61 (d, J=8.11 Hz, 1H), 7.80 (m, 2H); MS m/z (M+Na+) 372.10.

Provenance & Evidence