1-Bromo-4-(dimethoxymethyl)benzene → HCID 57142883, compound

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Reaction Steps

To a cooled (−78° C.) solution of 4-bromo-benzaldehyde dimethyl ketal (2.31 g 10 mmol) in THF (30 mL) is added, dropwise, n-butyl lithium (4.4 mL, 2.5 M in hexanes). On complete addition, the reaction mixture is stirred for 5 min then ZnCl2 solution (20 mL, 0.5M in THF) is added. The cold bath is removed and stirring continued for 5 min. then a solution comprising of 5-bromo-(2-[t-butyldiphenylsilyloxy]-pyrimidine (4.13 g, 10 mmol) and (Ph3P)4Pd (1.1 g, 1 mmol) in THF (20 mL) is added. This mixture is warmewd to 60° C. and stirred at this temperature for 2 h. The resulting solution is cooled to room temperature, diluted with ether, washed, sequentially, with 5% aqueous ammonia solution, water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 10% ethyl acetate, 10% dichloromethane in hexanes) to give 2.28 g of the title compound as an oil. 1H NMR (CDCl3) δ 1.18 (s, 9H), 3.35 (s, 6H), 5.44 (s, 1H), 7.38 (m, 6H), 7.44 (d, J=8 Hz, 2H), 7.53 (d, J=8 Hz, 2H), 7.8 (m, 4H), 8.59 (s, 2H).

Provenance & Evidence