Sodium hydride → (E)-1-iodo-3-[2-(4-methoxyphenyl)ethenyl]benzene

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Reaction Steps

To a mixture of NaH (2 mmol, 80% suspension in oil), and 3-iodobenzylphosphonate 13 (450 mg, 1.27 mmol) in 7 mL of THF at 80° C. under nitrogen atmosphere, was added dropwise p-anisaldehyde (172 mg, 1.27 mmol). After 3 days at room temperature, NH4Cl solution (saturated, 5 mL) was added and the mixture was extracted with CH2Cl2 (3×30 mL). The combined organic extract was dried over Na2SO4, evaporated and purified by flash chromatography (EtOAc: Hex, 1:9) to give (E)-1-iodo-3-[2-(4-methoxyphenyl)ethenyl] benzene 8 (400 mg, 90%). 1H NMR (200 MHz, CDCl3): δ 3.84 (s, 3H), 6.84 (d, J=16.29 Hz, 1H), 6.90 (m, 2H), 7.05 (d, J=16.30 Hz, 1H), 7.07 (t, J=7.8 Hz, 1H), 7.42–7.56 (m, 4H), 7.85 (s, 1H); 13C NMR (50 MHz, CDCl3): δ 55.32, 94.76, 114.20, 124.85, 125.48, 127.88, 129.58, 129.62, 130.25, 135.00, 135.91, 139.97, 159.62; HRMS: m/z Calcd for C15H13IO: 336.0011; Found: 336.0006.

Provenance & Evidence