Diisopropylethylamine → 3-(2-Methyl-5-nitrophenyl)furan

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-bromo-4-methyl nitrobenzene 1 (421 mg, 2.0 mmol), 3-furan boronic acid 2 (452 mg, 4.0 mmol), diisopropylethylamine (1.4 mL, 8.0 mmol), and Pd(dppf)Cl2—CH2Cl2 (162 mg, 0.2 mmol) in dry NMP (10 mL) was sparged with Ar for 20 min. The reaction mixture was heated to 80° C. and maintained at that temperature for 16 h. The reaction was allowed to cool to rt and was then partitioned with water and EtOAc. The resulting mixture was filtered through Celite and the phases partitioned and separated. The aqueous portion was extracted with EtOAc (3×) and the combined organic phases were washed with brine, dried (MgSO4), and concentrated. The crude residue was adsorbed onto SiO2 and purified by flash chromatography (9:1 hexanes-EtOAc) to furnish 319 mg (1.57 mmol, 80%) of an off-white solid as 3: 1H NMR (300 MHz, CD3OD) δ 8.16 (d, J=2.5 Hz, 1H), 8.04 (dd, J=2.5, 8.5 Hz, 1H), 7.77 (dd, J=0.8, 1.7 Hz, 1H), 7.63 (app t, J=1.9 Hz, 1H), 7.48 (d, J=8.5 Hz, 1H), 6.72 (dd, J=0.8, 1.9 Hz, 1H), 2.48 (s, 3H).

Provenance & Evidence