bromine; triphenylphosphine in acetonitrile T=50°C; 6 h;

1.1: 88 percent / BuLi; CuBr2; PhNO2 / hexane; diethyl ether / -75 - 25 °C 2.1: s-BuLi; N,N,N',N'',N''-pentamethyldiethylenetriamine / cyclohexane; tetrahydrofuran / 2 h / -100 - -75 °C 2.2: 79 percent / tetrahydrofuran; cyclohexane 3.1: s-BuLi; PMDTA / tetrahydrofuran; cyclohexane / 2 h / -100 - -75 °C 3.2: 82 percent / tetrahydrofuran; cyclohexane / 25 °C 4.1: 88 percent / NaBH4 / tetrahydrofuran; methanol / 12 h / 25 °C 5.1: 89 percent / Br2; Ph3P / acetonitrile / 6 h / 50 °C View Scheme

1.1: s-BuLi; N,N,N',N'',N''-pentamethyldiethylenetriamine / cyclohexane; tetrahydrofuran / 2 h / -100 - -75 °C 1.2: 79 percent / tetrahydrofuran; cyclohexane 2.1: s-BuLi; PMDTA / tetrahydrofuran; cyclohexane / 2 h / -100 - -75 °C 2.2: 82 percent / tetrahydrofuran; cyclohexane / 25 °C 3.1: 88 percent / NaBH4 / tetrahydrofuran; methanol / 12 h / 25 °C 4.1: 89 percent / Br2; Ph3P / acetonitrile / 6 h / 50 °C View Scheme

1.1: s-BuLi; PMDTA / tetrahydrofuran; cyclohexane / 2 h / -100 - -75 °C 1.2: 82 percent / tetrahydrofuran; cyclohexane / 25 °C 2.1: 88 percent / NaBH4 / tetrahydrofuran; methanol / 12 h / 25 °C 3.1: 89 percent / Br2; Ph3P / acetonitrile / 6 h / 50 °C View Scheme

1: 88 percent / NaBH4 / tetrahydrofuran; methanol / 12 h / 25 °C 2: 89 percent / Br2; Ph3P / acetonitrile / 6 h / 50 °C View Scheme