Hydrogen Peroxide → HCID 22287194, compound

Participants

Reaction Steps

In a four necked flask equipped with a stirrer, a reflux condenser and a thermometer which had been replaced by a nitrogen atmosphere, 4-(3-hydroxy-3,3-dimethyl-1-propynyl)-3-fluoro-1-bromobenzene (3.9 g, 15 mmol), bis(triphenylphosphine)palladium chloride (0.07 g, 0.1 mmol), sodium hydroxide (1.2 g, 30 mmol), tetrahydrofuran (40 ml) and N-methylpyrrolidone (5 ml) were charged. Then, to the mixture, a solution of E-1-pentenylcatecholborane prepared in Reference Example 1 (20 mmol) in tetrahydrofuran (50 ml) was dropwise added at room temperature, followed by heat refluxing for 6 hours while stirring. After cooling the reaction mixture to room temperature, 30% aqueous hydrogen peroxide (2 ml) was added to the mixture, followed by stirring for 1 hour. The mixture was extracted with toluene and water. The organic layer was washed with water twice and dried over anhydrous magnesium sulfate. After evaporating the solvent off, the residue was purified by silica gel column chromatography to obtain 4-(3-hydroxy-3,3-dimethyl-1-propynyl)-1-(1-trans-pentenyl)-3-fluorobenzene (3.1 g). Yield: 84%. Melting point: 62° C.

Provenance & Evidence