Multi-step reaction with 7 steps
1: 97 percent / K2CO3 / dimethylformamide / 18 h
2: 1.) 9-BBN, 2.) 3 M NaOH, 30percent H2O2 / 1.) THF, 65 deg C, 2.5 h, 2.) THF, below 28 deg C, 30 min
3: 88 percent / PPh3, collidine, CBr4 / CH2Cl2 / 2 h / -5 - -3 °C
4: 84 percent / Fe, NH4Cl / H2O; ethanol / 1.5 h / 65 - 70 °C
5: 60 percent / pyridine / tetrahydrofuran / 1.5 h / -60 - 10 °C
6: 70 percent / NaH, HMPA / tetrahydrofuran / 108 h / 35 °C
7: 70 percent / CF3COOH / 5 h / 50 °C
With
pyridine; 2,3,5-trimethyl-pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; carbon tetrabromide; dihydrogen peroxide; iron; sodium hydride; potassium carbonate; ammonium chloride; triphenylphosphine; trifluoroacetic acid;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00021a042