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

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Reaction Conditions

Reaction Steps

A mixture of 2.09 g (19.5 mmol) of 2-methylaniline, 4.00 g (13.0 mmol) of 2-[2-(bromomethyl)-6-methylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and 1.97 g (14.3 mmol) of K2CO3 in 75 ml of DMF was stirred for 12 h at the 80° C. The resulting mixture was poured into 300 ml of water. The product was extracted with 3×50 ml of ethyl acetate. The combined extract was dried over Na2SO4 and then evaporated to dryness. An excess of 2-methylaniline was distilled off using Kugelrohr apparatus. The residue was re-crystallized from 20 ml of hexane. Yield 2.60 g (59%) of light-yellow powder. Anal. calc. for C21H28BNO2: C, 74.79; H, 8.37; N, 4.15. Found: C, 74.95; H, 8.52; N, 3.95. 1H NMR (CDCl3): δ 7.22 (m, 1H, 3-H in 6-MeC6H3CH2), 7.16 (m, 1H, 3-H in 6-MeC6H3CH2), 7.12 (m, 1H, 5-H in 2-MeC6H4), 7.09 (m, 1H, 5-H in 6-MeC6H3CH2), 7.04 (m, 1H, 3-H in 2-MeC6H4), 6.71 (m, 1H, 6-H in 2-MeC6H4), 6.66 (m, 1H, 4-H in 2-MeC6H4), 4.34 (d, J=25.3 Hz, 1H, CHH′NH), 4.27 (d, J=25.3 Hz, 1H, CHH′NH), 3.85 (br.s, 1H, NH), 2.46 (s, 3H, Me in 6-MeC6H3CH2), 2.11 (s, 3H, Me in 2-MeC6H4), 1.25 (s, 12H, Bpin).

Provenance & Evidence