Diethylzinc (ca. 15% in Hexane, ca. 1mol/L)

• Ethyl 2-Iodobenzoate [E1273]
• Tridecafluorohexyl Iodide [T1098]
• Diethylzinc (ca. 15% in Hexane, ca. 1mol/L) [D3214]
• Copper(I) Iodide [C2163]
• DMPU [D2014]

To a solution of diethylzinc (ca. 1mol/L in hexane, 2.9 mL, 2.9 mmol) and tridecafluorohexyl iodide (0.92 mL, 4.2 mmol) in DMPU (1.2 mL) was added ethyl 2-Iodobenzoate (500 mg, 1.9 mmol) and copper(I) iodide (37 mg, 0.20 mmol) and the reaction mixture was stirred under nitrogen at 90 °C for 16 hours. The reaction was quenched with 4 mol/L HCl and extracted with diethyl ether. The organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, hexane:dichloromethane = 7:1) to give 1 as a colorless oil (804 mg, 92% yield).

The reaction mixture was monitored by NMR.

Ethyl 2-(1,1,2,2,3,3,4,4,5,5,6,6,6-Tridecafluorohexyl)benzoate (1)

¹H NMR (270 MHz, CDCl₃); δ 7.67-7.57 (m, 4H), 4.38 (q, J = 7.0 Hz, 2H), 1.35 (t, J = 7.0 Hz, 3H)

• Dialkylzinc-Mediated Cross-Coupling Reactions of Perfluoroalkyl and Perfluoroaryl Halides with Aryl Halides
• H. Kato, K. Hirano, D. Kurauchi, N. Toriumi, M. Uchiyama, Chem. Eur. J. 2015, 21, 3895.