反应详情

温度

90 °C

A solution of 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (0.210 g, 0.898 mmol) and 4-bromo-2-butoxy-benzaldehyde (0.210 g, 0.817 mmol) in 1,4-dioxane (20 mL) is evacuated and re-filled with N2 3 times. To this solution, Pd(PPh3)4 (0.010 g) and aqueous Na2CO3 (1.0 mL, 2.0 M) are added. The resulting mixture is heated at 90° C. for 24 hours under N2. The reaction mixture is cooled to room temperature, neutralized with HCl (1.0 M, 3.0 mL), and concentrated. The residue is extracted with ethyl acetate (30 mL×2), and the combined organic layers are dried over sodium sulfate and concentrated. The residue is purified via silica gel chromatography eluting with 25-30% ethyl acetate in hexanes to give the title compound (0.198 g, 85%). ES/MS m/e 283.0 (M−1).

1. temperatureThe reaction mixture is cooled to room temperature
2. concentrationconcentrated
3. extractionThe residue is extracted with ethyl acetate (30 mL×2)
4. dry with materialthe combined organic layers are dried over sodium sulfate
5. concentrationconcentrated
6. customThe residue is purified via silica gel chromatography
7. washeluting with 25-30% ethyl acetate in hexanes