Compound 1f

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Compound data: 1H NMR

Compound data: 13C NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

To a mixture of ethylboronic acid (0.734 g, 10.0 mmol), 2-bromobenzaldehyde (5.0 mmol), and K₂CO₃ (2.08 g, 15.0 mmol) in dry toluene (15 mL) was added PdCl₂(dppf) (183 mg, 0.25 mmol) under nitrogen. The resulting reaction mixture was heated under reflux for 6 h. Upon completion, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, filtered through Celite, and concentrated in vacuo. The crude residue was purified by flash chromatography to afford 1f, 1k, and 1l. ¹H NMR (600 MHz, CDCl₃): δ 10.34 (s, 1H), 8.68 (d, J = 2.5 Hz, 1H), 8.35 (dd, J = 8.4, 2.5 Hz, 1H), 7.51 (d, J = 8.4 Hz, 1H), 3.18 (q, J = 7.6 Hz, 2H), 1.33 (t, J = 7.6 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 189.93, 153.74, 146.72, 134.13, 131.57, 127.87, 126.42, 25.92, 15.83. HRMS (ESI-TOF): m/z calculated for C₉H₁₀NO₃⁺ [M+H]⁺ 180.0655, found 180.0652.