31786-46-6

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of methyl 2-bromo-6-methoxybenzoate (30 g, 0.12 mol) and potassium trifluoro(vinyl)borate (18 g, 0.13 mol) in dioxane and H2O (5:1, 360 mL) was added Pd(dppf)Cl2 (2.63 g, 0.0036 mol) and Na2CO3 (25.4 g, 0.24 mol) at RT. The reaction mixture was heated at 100° C. for 12 hours under a nitrogen atmosphere. The mixture was subsequently concentrated in vacuo, diluted with water, and extracted with EtOAc (3×100 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2CO3, filtered, and concentrated. The crude product was purified by column chromatography eluting with a gradient of petroleum ether (1-2%) and EtOAc to give the title compound (22 g, 95%). 1H NMR (400 MHz, CDCl3) δ ppm 7.33 (t, J=8.0 Hz, 1H), 7.18 (d, J=8.0 Hz, 1H), 6.85 (d, J=8.0 Hz, 1H), 6.67 (dd, J=11.0, 17.4 Hz, 1H), 5.75 (d, J=17.4 Hz, 1H), 5.35 (d, J=11.0 Hz, 1H), 3.93 (s, 3H), 3.84 (s, 3H); ESI-MS m/z [M+H]+ 193. The mixture was subsequently concentrated in vacuo diluted with water extracted with EtOAc (3×100 mL) washed with brine dried over anhydrous Na2CO3 filtered concentrated The crude product was purified by column chromatography eluting with a gradient of petroleum ether (1-2%) and EtOAc

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 2-bromo-6-methoxybenzoic acid (40 g, 0.176 mol) in DMF (300 mL) was added K2CO3 (24.8 g, 0.176 mol) and CH3I (37 g, 0.264 mol). The mixture was stirred at RT overnight. The reaction was quenched with 1M HCl aq and the mixture was extracted with EtOAc (3×300 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound (41 g, 99%). The reaction was quenched with 1M HCl aq the mixture was extracted with EtOAc (3×300 mL) The organic phase was dried over MgSO4 concentrated in vacuo