| 96% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; palladium diacetate; In toluene; at 120℃; for 24h; |
2-(4-Bromo-phenyl)-6-nnethoxy-benzofuran (550 mg; 1 ,81 mmol), <strong>[4737-50-2]pentylboronic acid</strong> (463 mg; 3,99 mmol) and tripotassium phosphate monohydrate (1 ,75 g; 7,62 mmol) are dissolved in toluene (19,2 ml; 181 mmol). Then 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl [SPhos] (149 mg; 359 muiotatauiotaomicronIota) and palladium(ll) acetate (40,7 mg; 180 muiotatauiotaomicronIota) are added and the reaction mixture is heated to 120 C for 1 d. The cooled reaction mixture is diluted with ethyl acetate and HCI solution (2 M). The solution is transferred to a separatory funnel. The organic phase is extracted with HCI solution (2 M) and water and brine. The organic phase is dried over MgS04, filtered and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (heptane/ethyl acetate, 5/1 ) to yield 6-Methoxy-2-(4-pentyl-phenyl)-benzofuran (512 mg; 1 ,7 mmol; 96% of theory). (0472) 1 H NMR (500 MHz, Chloroform-d) delta 7.65 (d, J = 8.2 Hz, 2H), 7.35 (d, J = 8.5 Hz, 1 H), 7.17 (d, J = 8.1 Hz, 2H), 6.99 (d, J = 2.1 Hz, 1 H), 6.82 (s, 1 H), 6.79 (dd, J = 8.5, 2.3 Hz, 1 H), 3.80 (s, 3H), 2.59 - 2.54 (m, 2H), 1 .58 (p, J = 7.5 Hz, 2H), 1 .32 - 1 .24 (m, 4H), 0.83 (t, J = 6.9 Hz, 3H). |
| 96% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; palladium diacetate; In toluene; at 120℃; for 24h;Inert atmosphere; |
2-(4-Bromo-phenyl)-6-methoxy-benzofuran (550 mg; 1,81 mmol), <strong>[4737-50-2]pentylboronic acid</strong> (463 mg; 3,99 mmol) and tripotassium phosphate monohydrate (1,75 g; 7,62 mmol) are dissolved in toluene (19,2 ml; 181 mmol). Then 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl [SPhos] (149 mg; 359 muiotatauiotaomicronIota) and palladium(ll) acetate (40,7 mg; 180 muiotatauiotaomicronIota) are added and the reaction mixture is heated to 120 C for 1 d. The cooled reaction mixture is diluted with ethyl acetate and HCI solution (2 M). The solution is transferred to a separatory funnel. The organic phase is extracted with HCI solution (2 M) and water and brine. The organic phase is dried over MgSO4, filtered and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (heptane/ethyl acetate, 5/1) to yield 6-Methoxy-2-(4-pentyl-phenyl)-benzofuran (512 mg; 1,7 mmol; 96% of theory). 1H NMR (500 MHz, Chloroform-d) delta 7.65 (d, J = 8.2 Hz, 2H), 7.35 (d, J = 8.5 Hz, 1H), 7.17 (d, J = 8.1Hz, 2H), 6.99 (d, J = 2.1Hz, 1H), 6.82 (s, 1H), 6.79 (dd, J = 8.5, 2.3 Hz, 1H), 3.80 (s, 3H), 2.59 - 2.54 (m, 2H), 1.58 (p, J = 7.5 Hz, 2H), 1.32 - 1.24 (m, 4H), 0.83 (t, J = 6.9 Hz, 3H). |
| 66% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; palladium diacetate; In toluene; at 120℃; for 24h; |
General procedure: 2-(4-Bromo-phenyl)-6-methoxy-benzofuran (550 mg, 1 .81 mmol), <strong>[4737-50-2]pentylboronic acid</strong> (463 mg, 3.99 mmol) and tripotassium phosphate monohydrate (1 .75 g, 7.62 mmol) are dissolved in toluene (19.2 ml, 181 mmol). Then 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl [SPhos] (149 mg, 359 muetaetaomicronIota) and palladium(ll) acetate (40.7 mg, 180 muetaetaomicronIota) are added and the reaction reaction mixture is heated to 120 C for 1 d. The cooled reaction mixture is diluted with ethyl acetate and HCI solution (2 M). The solution is transferred to a separatory funnel. The organic phase is extracted with HCI solution (2 M) and water and brine. The organic phase is dried over MgS04, filtered and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (heptane/ethyl acetate [5/1 ]) to yield 6-Methoxy-2-(4-pentyl-phenyl)-benzofuran (350 mg, 1 .2 mmol, 66% of theory).1 H NMR (500 MHz, Chloroform-d) delta 7.65 (d, J = 8.2 Hz, 2H), 7.35 (d, J = 8.5 Hz, 1 H), 7.17 (d, J = 8.1 Hz, 2H), 6.99 (d, J = 2.1 Hz, 1 H), 6.82 (s, 1 H), 6.79 (dd, J = 8.5 Hz, 2.3 Hz, 1 H), 3.80 (s, 3H), 2.59 - 2.54 (m, 2H), 1 .58 (p, J = 7.5 Hz, 2H), 1 .32 - 1 .24 (m, 4H), 0.83 (t, J = 6.9 Hz, 3H). |
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