p-Bromoacetophenone → HCID 53817625, compound

Participants

Reaction Steps

To a solution of 9-BBN (0.5 M in THF) (90.0 ml, 45.0 mmol) at 23° C., 1-pentene (4.93 ml, 45.0 mmol) was added. After 12 h, the solution was diluted with anhydrous dioxane (150 ml) and then 4-bromoacetophenone (5.97 g, 30.0 mmol) K3PO4 (9.55 g, 45.0 mmol), Pd(PPh3)4 (0.867 g, 0.750 mmol) were added. After deoxygenating the solution with N2 for 20 min, the solution was refluxed for 12 h. After cooling to ambient temperature, 3N NaOH (40 ml) and 30% H2O2 (40 ml) were added dropwise followed by dilution with hexanes (200 ml). After separation of layers, the organic layer was washed with brine (200 ml), dried, and concentrated under reduced pressure. The crude product was purified by flash chromatography eluting with 10% EtOAc/hexanes, to afford 4.09 g of 11 as an oil (72%). 1H NMR (CDCl3) δ 0.88 (t, J=6.9 Hz, 3H), 1.23-1.36 (m, 4H), 1.55-1.69 (m, 2H), 2.58 (s, 3 H), 2.66 (t, J=7.7 Hz, 2H), 7.25 (d, J=1.9 Hz, 2H), 7.86 (d, J=1.9 Hz, 2H); 13C NMR (CDCl3) δ 14.09, 22.58, 26.65, 30.89, 31.51, 36.04, 128.55, 128.68, 134.97, 148.92, 197.98.

Provenance & Evidence