Benzyl Bromide → 2-(Benzyloxy)-4-bromo-1-methoxybenzene

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NaH, 60% dispersion in mineral oil (0.61 g, 15.3 mmol) was added in three equal portions to DMF (25 mL) pre-cooled to 0° C. 5-Bromo-2-methoxyphenol (2.60 g, 12.8 mmol) was then added in three portions, and the resulting brown solution was stirred for 20 min. Benzyl bromide (2.63 g, 15.3 mmol) was added and the reaction mixture was allowed to warm to room temperature and was stirred overnight resulting in the formation of a yellow solution. The reaction mixture was poured onto H2O (40 mL) leading to the formation of a white precipitate which was extracted into EtOAc (4×50 mL). The combined organics were washed with H2O (4×75 mL), brine (75 mL), dried (MgSO4) and the solvent was removed in vacuo. The crude product was obtained as a white solid which was purified by recrystallisation from Et2O to give the title compound (2.90 g, 77%, mp 109-110° C. [lit. 105-106° C. (Et2O)]Aust. J. Chem., 1981, 34 587) as a white crystalline solid; δH (270 MHz, CDCl3) 7.47-7.26 (5H, m, ArH), 7.07-7.00 (2H, m, ArH), 6.74 (1H, d, J=8.7, ArH), 5.10 (2H, s, CH2), 3.85 (3H, s, CH3), LRMS (FAB+) 294.0 ([M+H]+, 35%), 292.0 (35), 91.1 (100).

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