Multi-step reaction with 9 steps
1: 95 percent / sodium borohydride / methanol
2: 81 percent / phosphorus tribromide / CH2Cl2 / -5 °C
3: 87 percent / sodium cyanide / dimethylsulfoxide
4: 64 percent / sodium hydride / dimethylformamide / 2 h
5: 82 percent / hydrochloric acid / acetic acid; H2O / 6 h / Heating
6: 36 percent / methanesulphonyl chloride / pyridine / 1.17 h / Heating
7: H2 / 10percent Pd/C / acetic acid / 1 h / 2585.7 Torr
8: 1.) sulphuric acid, sodium nitrite, 2.) potassium iodide,iodine, urea / 1.) water, -10 deg C, 2.) chloroform, water, RT, 1-2 h
9: 1.) boron tribromide, 2.) 2M-NaOH / 1.) methylene dichloride, 0 deg C, RT, 1.5 h, 2.) 100 deg C, 0.25 h
With
hydrogenchloride; sodium cyanide; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; hydrogen; iodine; boron tribromide; phosphorus tribromide; sodium hydride; methanesulfonyl chloride; urea; potassium iodide; sodium nitrite;
palladium on activated charcoal;
In
pyridine; methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1039/P19880003085