4-Fluoro-2-nitro-1-(prop-1-en-2-yl)benzene → 5-Fluoro-2-isopropylaniline

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To 4-fluoro-2-nitro-1-(prop-1-en-2-yl)benzene (0.837 g, 4.62 mmol) in a 250 mL round-bottomed flask equipped with a stir bar and rubber septum was added EtOAc (46.2 ml) followed by palladium on carbon (0.983 g, 0.462 mmol). The reaction was evacuated and purged with hydrogen (balloon) (2×) and stirred under hydrogen at room temperature overnight. The reaction was determined to be complete by TLC (10% EtOAc/Hex). The mixture was filtered through Celite, washed with EtOAc and concentrated. 5-Fluoro-2-isopropylaniline (673 mg, 4.40 mmol, 95%) was obtained as a clear and yellow oil: IR (thin film) 3480 (w), 3390 (w), 2962 (m), 2872 (w), 1622 (m), 1504 (s), 1431 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 7.05 (dd, J=8.5, 6.4 Hz, 1H), 6.45 (td, J=8.5, 2.6 Hz, 1H), 6.37 (dd, J=10.6, 2.6 Hz, 1H), 3.74 (bs, 2H), 2.83 (hept, J=6.8 Hz, 1H), 1.24 (d, J=6.8 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 161.75 (d, JCF=241.3 Hz), 144.76 (d, JCF=10.3 Hz), 128.11 (d, JCF=2.8 Hz), 126.53 (d, JCF=9.6 Hz), 105.06 (d, JCF=20.7 Hz), 102.26 (d, JCF=24.2 Hz), 27.27, 22.35.

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