Multi-step reaction with 7 steps
1: 69.9 percent / POCl3 / 3 h / Heating
2: 91.1 percent / H2O / 3 h / Heating
3: 1.) NaNO2, AcOH, 2.) 35percent HNO3 / 1.) H2O, 5 deg C, 1.5 h, 2.) a) 5 deg C, 0.5 h, b) reflux, 1 h
4: Fe, HCl / ethanol; H2O / 0.5 h / Heating
5: 56.3 percent / Br2 / acetic acid; trifluoroacetic acid / 1.) ice-bath temperature, 1.5 h, 2.) ice-bath temperature -> room temperature
6: T2 / 10percent Pd/C / 2 h
7: 1.) NaNO2, N HCl, 2.) NaN3 / 1.) H2O, 0 deg C, 10 min, 2.) 0 deg C, 1 h
With
hydrogenchloride; sodium azide; tritium; water; bromine; nitric acid; iron; acetic acid; sodium nitrite; trichlorophosphate;
palladium on activated charcoal;
In
ethanol; water; acetic acid; trifluoroacetic acid;
DOI:10.1021/jm00128a022