Water → 2-Methyl-N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline

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Reaction Conditions

Reaction Steps

A mixture of 8.75 g (63.4 mmol) of K2CO3, 9.25 g (86.4 mmol) of 2-methylaniline and 20.0 g (57.6 mmol) of 2-[2-(bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in 450 ml of DMF was stirred at 80° C. for 12 h. The resulting mixture was poured into 100 cm3 of water, and the product was extracted with 3×250 ml of ethyl acetate. The combined organic extract was dried over MgSO4 and then evaporated to dryness. Crystallization of this crude product from 250 ml of hexanes gave 14.4 g (67%) of brown crystals of the title compound. Anal. Calc. for C24H2813NO2: C, 77.22; H, 7.56; N, 3.75. Found: C, 77.39; H, 7.70; N, 3.64. 1H NMR (CDCl3): 8.20 (m, 1H, 8-H in naphthyl), 7.84 (d, J=8.5 Hz, 1H, 4-H in naphthyl), 7.82 (m, 1H, 5-H in naphthyl), 7.43-7.52 (m, 3H, 3,6,7-H in naphthyl), 7.14 (m, 1H, 5-H in Ph), 7.06 (m, 1H, 3-H in Ph), 6.79 (m, 1H, 6-H in Ph), 6.68 (m, 1H, 4-H in Ph),

Provenance & Evidence