反应详情

A suspension of methyl 4-bromo-3-methylbenzoate (4.9 g; 21.4 mmol; 1 eq.), 2-methoxyphenylboronic acid (Aldrich 44, 523-1; 3.6 g; 23.5 mmol; 1.1 eq.), potassium carbonate (14.8 g; 107 mmol; 5 eq.) and Pd(PPh3)4 (2.47 g; 2.14 mmol; 0.1 eq.) in toluene (24.5 mL) and water (24.5 mL) was refluxed for 6 hours. The reaction mixture was cooled down to room temperature and filtered through a pad of CELITE which was further washed with toluene (500 mL). The filtrate was concentrated in vacuo and the residue taken up in ethyl acetate (500 mL). The organic layer was washed with sat. aq. NaHCO3 (200 mL), water (200 mL) and brine (200 mL) then dried over magnesium sulfate and concentrated in vacuo. The crude was purified by column chromatography (c-hexane/ethyl acetate, 90/10) to afford the title compound (4.38 g, 80%) as a colorless oil. HPLC (Method A): Rt 4.85 min (purity 98.9%). LC/MS: 257.0 (M+H)+.

1. temperaturewas refluxed for 6 hours
2. filtrationfiltered through a pad of CELITE which
3. washwas further washed with toluene (500 mL)
4. concentrationThe filtrate was concentrated in vacuo
5. washThe organic layer was washed with sat. aq. NaHCO3 (200 mL), water (200 mL) and brine (200 mL)
6. dry with materialthen dried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customThe crude was purified by column chromatography (c-hexane/ethyl acetate, 90/10)