Allyl Alcohol → 3-(4-Bromo-2-methylphenyl)propanal

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 1.00 g (3.39 mmol) of 4-bromo-1-iodo-2-methylbenzene, 0.58 g (10.00 mmol) of allyl alcohol, 0.69 g (8.20 mmol) of sodium bicarbonate, 0.92 g (3.30 mmol) of tetrabutylammonium chloride, and 22 mg (0.10 mmol) of palladium (II) acetate in 5 mL of DMF were stirred for 16 hours at 45° C. under argon. The reaction mixture was diluted with EtOAc, and the organic phase was washed with water, dried over magnesium sulfate, and evaporated down in vacuo. The residue was purified by column chromatography (silica gel, PE/EtOAc 4:1). Yield: 0.60 (78% of theoretical); C10H11BrO (M=227.098); calc.: molpeak (M+H)+: 226/228 (Br); found: molpeak (M+H)+: 226/228 (Br); Rf value: 0.45 (silica gel, PE/EtOAc 4:1).

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