Water → HCID 59353046, compound

Participants

Reaction Steps

To a solution of 1-iodo-4-methoxy-2-nitrobenzene (5 g, 18 mmol) in. THF (500 mL) are added cesium fluoride (11 g, 72 mmol) and Pd(PPh3)4(0.56 g, 48 mmol). The resulting mixture is stirred for 30 min at room temperature. A solution of allylboronic acid pinacol ester (5.6 mL, 33 mmol) in THF (15 mL) is added dropwise. The resulting mixture is refluxed for 24 h then diluted with hexane (100 mL) followed by water (100 mL). The product is extracted with hexane (2×100 mL). The combined organic layers are washed with water (150 mL) then brine (150 mL) and dried over Na2SO4. The solvent is removed under reduced pressure and the residue is purified by column chromatography using hexane as eluent affording 1.8 g (48%) of the title compound as a brown liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.93-7.91 (m, 1), 7.59-7.50 (m, 1H), 7.04-7.01 (m, 1H), 5.0-4.9 (m, 2H), 3.89-3.85 (m, 1H), 3.81 (s, 3H), 3.53-3.51 (m, 2H).

Provenance & Evidence