Dichloromethane → HCID 69589285, compound

Participants

Reaction Steps

A mixture of 5-Isopropenyl-4-isopropyl-2-(4-trifluoromethyl-phenyl)-oxazole (0.5 g, 1.695 mmol), 9-BBN dimer (0.46 g, 1.865 mmol), and tetrahydrofuran (5 mL) is stirred at room temperature 6 hr. The mixture is diluted with water (1 mL). In another flask, a mixture of (4-bromo-2-methyl-phenoxy)-acetic acid methyl ester (0.53 g, 2.03 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.14 g, 0.17 mmol), triphenylarsine (0.1 g, 0.339 mmol), and N,N-dimethylformamide (5 mL) is stirred in ice/water. The previously described 9-BBN solution is added via cannula and the resulting mixture is stirred at room temperature 18 hr. The black reaction mixture is diluted with water (50 mL) and brine (50 mL), and the product is extracted to ethyl acetate (3×75 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, and concentrated. The black residue is purified via silica chromatography eluting with 1:1 hexanes:dichloromethane to 1:1:0.5 hexanes:dichloromethane:ethyl acetate to afford the product as a colorless oil, 0.136 g, 17%. MS M++1 476. The structure is confirmed by 1H NMR spectroscopy.

Provenance & Evidence