反应详情

Methyl 4-bromo-3-(methoxymethyl)benzoate (40 g; 154.38 mmol; 1 eq.), o-tolylboronic acid (23.09 g; 169.82 mmol; 1.10 eq.), K2CO3 (106.68 g; 771.90 mmol; 5 eq.), tetrakis(triphenylphosphine)palladium (0) (1.78 g; 1.54 mmol; 0.01 eq.) 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 (1000 mL). The filtrate was concentrated to afford 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 (41.9 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 (1000 mL)
6. concentrationThe filtrate was concentrated
7. customto afford 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