反应详情

Methyl 4-bromo-3-(methoxymethyl)benzoate, (40 g; 154 mmol), o-tolylboronic acid (23 g; 170 mmol), K2CO3 (107 g; 772 mmol), tetrakis(triphenylphosphine)palladium (0) (1.8 g; 1.5 mmol) were taken up in toluene (200 mL) and water (200 mL) under N2 atmosphere. The reaction mixture was purged with vacuum, then degassed with N2 and then refluxed for 1 hour. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with EtOAc (1 L). The filtrate was concentrated, affording a yellow oil which was taken in EtOAc (800 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 solution (250 mL), water (250 mL) and brine (250 mL), dried over MgSO4 and concentrated affording the title compound as a yellow oil used without further purification (42 g, quantitative). HPLC (Method A) Rt 5.34 min (Purity: 89.4%).

1. customThe reaction mixture was purged with vacuum
2. customdegassed with N2
3. temperaturerefluxed for 1 hour
4. filtrationfiltered over a pad of celite
5. washwashed with EtOAc (1 L)
6. concentrationThe filtrate was concentrated
7. customaffording a yellow oil which
8. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 solution (250 mL), water (250 mL) and brine (250 mL)
9. dry with materialdried over MgSO4
10. concentrationconcentrated