Multi-step reaction with 6 steps
1: 1.) n-BuLi / 1.) Et2O, hexane, -70 deg C, 2.) Et2O, hexane, THF, -70 deg C, 1 h
2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 45 min, 2.) CH2Cl2, from -70 deg C to 25 deg C
3: 1.) dimsylsodium / 1.) DMSO, 20 min, 2.) DMSO, 4 h
4: 48percent aq. HBr / 4 h / Heating
5: SOCl2 / 3 h / Ambient temperature
6: 18 percent / NaH, KI / dimethylformamide / 18 h / 60 °C
With
n-butyllithium; thionyl chloride; oxalyl dichloride; dimsylsodium; hydrogen bromide; sodium hydride; dimethyl sulfoxide; triethylamine; potassium iodide;
In
N,N-dimethyl-formamide;
DOI:10.1021/jm00010a005