反应详情

温度

80 °C

A mixture of 29.2 g (216 mmol) of 2,4,6-trimethylaniline, 50.0 g (144 mmol) of 2-[2-(bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and 22.0 g (159 mmol) of K2CO3 in 1100 cm3 of DMF was stirred for 12 h at 80° C. The resulting mixture was poured into 2000 cm3 of water. The product was extracted with 3×400 ml of ethyl acetate. The combined extract was dried over MgSO4 and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane). Yield 45.0 g (78%). Anal. calc. for C26H32BNO2: C, 77.81; H, 8.04; N, 3.49. Found: C, 78.00; H, 8.24; N, 3.26. 1H NMR (CDCl3): δ 8.27 (m, 1H, 8-H in naphthyl), 7.84 (m, 1H, 5-H in naphthyl), 7.81 (d, J=8.3 Hz, 1H, 4-H in naphthyl), 7.54 (m, 1H, 7-H in naphthyl), 7.48 (m, 1H, 6-H in naphthyl), 7.37 (d, J=8.3 Hz, 1H, 3-H in naphthyl), 6.87 (s, 2H, 3, 5-H in mesityl), 4.39 (s, 2H, CH2N), 3.68 (br.s, 1H, NH), 2.31 (s, 6H, 2, 6-Me in mesityl), 2.30 (s, 3H, 4-Me in mesityl), 1.49 (s, 12H, Me in tetramethyldioxaborolane).

1. extractionThe product was extracted with 3×400 ml of ethyl acetate
2. extractionThe combined extract
3. dry with materialwas dried over MgSO4
4. customevaporated to dryness
5. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane)