4-Fluoroiodobenzene → HCID 15342619, compound

Participants

Reaction Steps

2-(Benzhydrylidene-amino)-3-(4′-fluoro-biphenyl-4-yl)-propionic acid ethyl ester is prepared according to the general procedure reported by Satoh et al. (Tetrahedron Letter Vol. 48, 7645 (1997)). A 50-mL flask is charged with the boronate intermediate of step 1 (600 mg, 1.01 mmol), 1-fluoro-4-iodo-benzene (247 mg, 1.11 mmol), PdCl2(dppf) (37 mg, 0.051 mmol), K3PO4 (860 mg, 4.04 mmol), and 10 mL of DME. The reaction mixture is heated at reflux for 12 hours then cooled to room temperature, and partitioned between EtOAc and water. The organic phase is separated and washed with brine, dried over MgSO4, filtered, and concentrated. The residue is purified by chromatography on silica gel (gradient elution with 5-10% EtOAc/hexane) to furnish the above imine as a light brown oil. 1H NMR (300 MHz, CDCl3) δ 7.50-7.70 (m, 4H), 7.25-7.40 (m, 8H), 7.05-7.20 (m, 4H), 6.55-6.70 (m, 2H), 4.15-4.30 (m, 3H), 3.15-3.35 (m, 2H), 1.15-1.25 (two t, 3H).

Provenance & Evidence