Water → 2-Methyl-N-[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 1.60 g (15 mmol) of 2-methylaniline, 3.00 g (10 mmol) of 2-[2-(bromomethyl)-phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and 1.52 g (11 mmol) of K2CO3 in 75 ml of DMF was stirred for 12 h at 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 n-hexane. Yield 1.82 g (56%) of red crystalline powder. Anal. calc. for C20H26BNO2: C, 74.32; H, 8.11; N, 4.33. Found: C, 73.99; H, 8.02; N, 4.45. 1H NMR (CDCl3): δ 7.82 (m, 1H, 5-H in 2-MeC6H4), 7.36-7.41 (m, 2H, 3, 5-H in C6H4CH2), 7.26 (m, 1H, 4-H in C6H4CH2), 7.08 (m, 1H, 5-H in 2-MeC6H4), 7.02 (m, 1H, 3-H in 2-MeC6H4), 6.71 (m, 1H, 6-H in 2-MeC6H4), 6.61 (m, 1H, 4-H in 2-MeC6H4), 4.55 (br.s, 2H, CH2NH), 4.31 (br.s, 1H, NH), 2.13 (s, 3H, Me in 2-MeC6H4), 1.31 (s, 12H, Bpin).

Provenance & Evidence