1: Br2 / CH2Cl2 / 0 °C 2: nBu4NF / tetrahydrofuran / 0 °C 3: imidazole / dimethylformamide / 0 - 20 °C 4: 94 percent / Pd(PPh3)4, CuI, nPrNH2 / benzene / 20 °C 5: 90 percent / KCN, AgNO3, / ethanol; tetrahydrofuran; H2O / 0 °C 6: 1.) disiamylborane, 2.) aq. 2N NaOH, Pd(PPh3)4 / 1.) THF,0 deg C, 1h; 2.) 50 deg C, 16 h 7: 80 percent / nBu4NF / tetrahydrofuran / 18 h / 25 °C View Scheme

1: Br2 / CH2Cl2 / 0.17 h / -70 °C 2: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C 3: imidazole / dimethylformamide / 5 h / Ambient temperature 4: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 5: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 6: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 7: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: Br2 / CH2Cl2 / 0.17 h / -70 °C 2: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C 3: imidazole / dimethylformamide / 5 h / Ambient temperature 4: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 5: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 6: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 7: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

Multi-step reaction with 2 steps 1: Br2 / CH2Cl2 / 0 °C2: nBu4NF / tetrahydrofuran / 0 °C  

Multi-step reaction with 3 steps 1: Br2 / CH2Cl2 / 0 °C2: nBu4NF / tetrahydrofuran / 0 °C3: imidazole / dimethylformamide / 0 - 20 °C  

Multi-step reaction with 4 steps 1: Br2 / CH2Cl2 / 0 °C2: nBu4NF / tetrahydrofuran / 0 °C3: imidazole / dimethylformamide / 0 - 20 °C4: 94 percent / Pd(PPh3)4, CuI, nPrNH2 / benzene / 20 °C  

Multi-step reaction with 5 steps 1: Br2 / CH2Cl2 / 0 °C2: nBu4NF / tetrahydrofuran / 0 °C3: imidazole / dimethylformamide / 0 - 20 °C4: 94 percent / Pd(PPh3)4, CuI, nPrNH2 / benzene / 20 °C5: 90 percent / KCN, AgNO3, / ethanol; tetrahydrofuran; H2O / 0 °C  

Multi-step reaction with 6 steps 1: Br2 / CH2Cl2 / 0 °C2: nBu4NF / tetrahydrofuran / 0 °C3: imidazole / dimethylformamide / 0 - 20 °C4: 94 percent / Pd(PPh3)4, CuI, nPrNH2 / benzene / 20 °C5: 90 percent / KCN, AgNO3, / ethanol; tetrahydrofuran; H2O / 0 °C6: 1.) disiamylborane, 2.) aq. 2N NaOH, Pd(PPh3)4 / 1.) THF,0 deg C, 1h; 2.) 50 deg C, 16 h