carbon tetrabromide; triphenylphosphine in dichloromethane T=0°C;

Yield given. Multistep reaction;

1: 75 percent / CuI, nBu4NI, Na2CO3 / dimethylformamide / Ambient temperature 2: 89 percent / H2, Ni(OAc)2, NaBH4 / Ambient temperature 3: 1.) MsCl, Et3N, 2.) NaI / 1.) CH2Cl2, RT, 2.) acetone, reflux 4: 99 percent / acetonitrile / Heating 5: 63 percent / n-BuLi, HMPA / tetrahydrofuran / -78 °C 6: 90 percent / n-Bu4NF*THF / acetic acid / Ambient temperature 7: MnO2 / diethyl ether / Ambient temperature View Scheme

Yield given. Multistep reaction;

2: 1.) H2, 2.) CBr3, Ph3P / 1.) Lindlar / 1.) CH2Cl2, 25 deg C, 2.) CH2Cl2, 0 deg C View Scheme