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 10.8 g (101 mmol) of 2-methylaniline, 23.3 g (67.0 mmol) of 2-[2-(bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and 10.2 g (74.0 mmol) of K2CO3 in 450 cm3 of DMF was stirred for 12 h at 80° C. The resulting mixture was poured into 1000 cm3 of water. The product was extracted with 3×200 ml of ethyl acetate. The combined extract was dried over MgSO4 and then evaporated to dryness. The residue was re-crystallized from a mixture of 200 ml of hexane and 10 ml of ethyl acetate. Yield 15.7 g (63%) of brown crystalline powder. Anal. calc. for C24H28BNO2: C, 77.22; H, 7.56; N, 3.75. Found: C, 77.33; H, 7.67; N, 3.59. 1H NMR (CDCl3): δ 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), 7.42-7.52 (m, 3H, 3, 6, 7-H in naphthyl), 7.14 (m, 1H, 5-H in 2-MeC6H4), 7.05 (m, 1H, 3-H in 2-MeC6H4), 6.78 (m, 1H, 6-H in 2-MeC6H4), 6.68 (m, 1H, 4-H in 2-MeC6H4), 4.53 (s, 2H, CH2NH), 3.95 (br.s, 1H, NH), 2.11 (s, 3H, Me), 1.36 (s, 12H, BPin).

Provenance & Evidence