Hydrochloric Acid → HCID 22934574, compound

Participants

Reaction Steps

To a solution (25 ml) of 2-(4-trifluoromethylphenyl)furan (3.18 g) in tetrahydrofuran was added dropwise n-butyl lithium (1.6 M solution in hexane, 10.0 ml) under an argon atmosphere at −78° C. This mixed solution was heated to room temperature, and a solution (30 ml) of zinc chloride (2.25 g) in tetrahydrofuran was added. This mixture was stirred for 1 hr., and then ethyl 2-bromobenzoate (2.38 ml) and tetrakis (triphenylphosphine)palladium (0.433 g) were added. This mixture was stirred overnight under an argon atmosphere, and then poured into 0.5 M hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, volume ratio) to give ethyl 2-[5-(4-trifluoromethylphenyl)-2-furyl]benzoate (2.54 g, yield 47%) as a pale-yellow oil. NMR (CDCl3) δ: 1.12 (3H, t, J=7.2 Hz), 4.27 (2H, q, J=7.2 Hz), 6.70 (1H, d, J=3.6 Hz), 6.87 (1H, d, J=3.6 Hz), 7.41 (1H, dt, J=1.4, 7.4 Hz), 7.53 (1H, dt, J=1.4, 7.4 Hz), 7.61–7.79 (6H, m).

Provenance & Evidence