反应详情

温度

80 °C

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),

1. extractionthe product was extracted with 3×250 ml of ethyl acetate
2. extractionThe combined organic extract
3. dry with materialwas dried over MgSO4
4. customevaporated to dryness
5. customCrystallization of this crude product from 250 ml of hexanes