1-Fluoro-2-nitro-3-(prop-1-en-2-yl)benzene → 2-Fluoro-6-isopropylaniline
反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:10])=[CH2:9])[C:3]=1[N+:11]([O-])=O>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[C:3]=1[NH2:11]参加物
4
実験手順
To a solution of 1-fluoro-2-nitro-3-(prop-1-en-2-yl)benzene (0.590 g, 3.26 mmol) in ethyl acetate (32.6 mL) in a 250 mL round-bottomed flask equipped with a magnetic stir bar and nitrogen inlet was added palladium on carbon (5% Pd/C, 0.693 g, 0.326 mmol). The reaction flask was evacuated and purged with hydrogen (2×) and then placed under 1 atmosphere (atm) of hydrogen and stirred at room temperature overnight. The reaction was filtered through Celite® and the pad was washed with ethyl acetate. The filtrate was concentrated to give the title compound (0.423 g, 2.76 mmol, 85% yield) as clear and colorless oil: IR (neat) 3476 (m), 3392 (m), 2966 (m), 2872 (m), 1628 (s), 1474 (s), 1270 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 6.92 (dt, J=7.7, 1.2 Hz, 1H), 6.86 (ddd, J=10.8, 8.1, 1.4 Hz, 1H), 6.69 (td, J=8.0, 5.6 Hz, 1H), 3.71 (bs, 2H), 2.92 (hept, J=6.8 Hz, 1H), 1.26 (d, J=6.8 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 151.91 (d, J=237.6 Hz), 135.10 (d, J=2.3 Hz), 131.60 (d, J=11.8 Hz), 120.52 (d, J=3.0 Hz), 117.99 (d, J=8.0 Hz), 112.28 (d, J=19.6 Hz), 27.77 (d, J=2.9 Hz), 22.22.