Cl[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.[CH3:24][C:25]1(C)[C:29](C)(C)OB(C(C)=C)O1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:25]([CH3:29])=[CH2:24])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1To 1-chloro-4-fluoro-2-nitrobenzene (1.03 g, 5.87 mmol) in a 100 mL round-bottomed flask equipped with a stir bar and nitrogen was added sodium carbonate (0.746 g, 7.04 mmol), dioxane (23.47 ml) and water (5.87 ml). To this was added 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (1.323 ml, 7.04 mmol) followed by bis(triphenylphosphine)palladium(II)chloride (0.329 g, 0.469 mmol). The reaction mixture was evacuated and backfilled with nitrogen (3×). The reaction was heated to 80° C. overnight. The reaction was determined to be complete by TLC (10% EtOAc/Hex). The reaction was cooled, filtered through Celite, washed with EtOAc and concentrated. The residue was taken up in dichloromethane, poured through a phase separator and concentrated. Purification by flash column chromatography provided the title compound 4-fluoro-2-nitro-1-(prop-1-en-2-yl)benzene (0.837 g, 75%) as a yellow oil: IR (thin film) 3091 (w), 2979 (w), 2918 (w), 1642 (w), 1530 (s), 1350 (s) cm−1; 1H NMR (400 MHz, CDCl3) δ 7.60 (dd, J=8.2, 2.5 Hz, 1H), 7.37-7.21 (m, 2H), 5.19 (p, J=1.5 Hz, 1H), 4.97-4.89 (m, 1H), 2.11-2.04 (m, 3H); 13C NMR (101 MHz, CDCl3) δ 160.96 (d, JCF=250.8 Hz), 148.46, 141.88, 135.18 (d, JCF=4.1 Hz), 132.09 (d, JCF=7.8 Hz), 119.98 (d, JCF=20.9 Hz), 115.99, 111.63 (d, JCF=26.4 Hz), 23.35.
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