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With phosphorus tribromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere
Into a 100-mL round-bottom flask, was placed 8-methylquinolin-4-ol (500 mg, 3.14 mmol, 1.00 equiv), N,N-dimethylformamide (20 mL). This was followed by the addition of tribromophosphane (851 mg, 3.14 mmol, 1.20 equiv) dropwise with stirring at room temperature. The resulting solution was stirred for 15 hours at room temperature. The reaction was then quenched by the addition of water/ice (100 mL). The pH value of the solution was adjusted to 10 with NaOH (2 mol/L). The precipitated solids were collected by filtration. This resulted in 660 mg (95percent) of 4-bromo-8-methylquinoline as a light yellow solid. MS (ES, m/z) [M+l] : 222&224.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In methanol; at 80.0℃; under 45603.1 Torr; for 16.0h;
Into a 50-mL pressure tank reactor, was placed <strong>[36075-68-0]4-bromo-8-methylquinoline</strong> (600 mg, 2.70 mmol, 1.00 equiv), Pd(dppf)Cl2 (444 mg, 0.54 mmol, 0.20 equiv), TEA (1.4 g, 13.86 mmol, 5.00 equiv), methanol (15 mL). The flask was evacuated and flushed three times with nitrogen, followed by flushing with carbon monoxide (60 atm). The resulting solution was stirred for 16 hours at 80 C. After cooled to room temperature, the solvent was removed under vacuum, the residue was re -dissolved in ethyl acetate (20 mL), washed by brine (20 mL x 3) and then applied onto a silica gel column with hexane/ethyl acetate (0- 30%). This resulted in 350 mg (64%) of methyl 8-methylquinoline-4-carboxylate as a white solid. MS (ES, m/z) [M+l] : 202.
64%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; at 80.0℃; for 16.0h;
Into a 50-mL pressure tank reactor (CO, 60 atm), was placed <strong>[36075-68-0]4-bromo-8-methylquinoline</strong> (600 mg, 2.70 mmol, 1.00 equiv), PdidppQChClrhCk (444 mg, 0.54 mmol, 0.20 equiv), TEA (1.4 g, 13.86 mmol, 5.00 equiv), methanol (15 mL). The resulting solution was stirred for 16 h at 80C. After cooling to room temperature, the reaction mixture was concentrated and the residue was applied onto a silica gel column with ethyl acetate/hexane (0-30%). This resulted in 350 mg (64%) of methyl 8-methylquinoline- 4-carboxylate as a white solid. MS (ES, m/z) [M+H]+: 202.
With phosphorus tribromide; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;
Into a 100-mL round-bottom flask, was placed <strong>[23432-44-2]8-methylquinolin-4-ol</strong> (500 mg, 3.14 mmol, 1.00 equiv), N,N-dimethylformamide (20 mL). This was followed by the addition of tribromophosphane (851 mg, 3.14 mmol, 1.20 equiv) dropwise with stirring at room temperature. The resulting solution was stirred for 15 hours at room temperature. The reaction was then quenched by the addition of water/ice (100 mL). The pH value of the solution was adjusted to 10 with NaOH (2 mol/L). The precipitated solids were collected by filtration. This resulted in 660 mg (95%) of 4-bromo-8-methylquinoline as a light yellow solid. MS (ES, m/z) [M+l] : 222&224.
95%
With phosphorus tribromide; In N,N-dimethyl-formamide; at 20℃; for 15.0h;
Into a lOO-mL round-bottom flask, was placed <strong>[23432-44-2]8-methylquinolin-4-ol</strong> (500 mg, 3.14 mmol, 1.00 equiv), N,N-dimethylformamide (20 mL). This was followed by the addition of tribromophosphane (851 mg, 3.14 mmol, 1.20 equiv) dropwise with stirring at room temperature. The resulting solution was stirred for 15 h at room temperature. The reaction was then quenched by the addition of water/ice (100 mL). The pH value of the solution was adjusted to 10 with sodium hydroxide (2 mol/L). The solids were collected by filtration. This resulted in 660 mg (95%) of 4-bromo-8-methylquinoline as a light yellow solid. MS (ES, m/z) [M+H]+: 222.
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