Multi-step reaction with 7 steps
1: 1.) sodium nitrite, conc. H2SO4, 2.) copper(I)bromide, hydrogen bromide / 1.) methanol, water, 0 deg C, 30 min, 2.) methanol, water, reflux, 1 h
2: 100 percent / activated carbon, ferric chloride hexahydrate, hydrazine hydrate / methanol / 12 h / Heating
3: 1.) sodium nitrite, conc. HCl, 2.) potassium iodide / 1.) water, 0 deg C, 20 min, 2.) water, RT, overnight
4: 78 percent / pyridine / 12 h / Heating
5: 1.) n-butyllithium / 1.) hexane, ether, -78 deg C, 20 min, 2.) hexane, ether, from -78 deg C to 0 deg C, 2 h
6: 75 percent / pyridinium chlorochromate, 3-A molecular sieves / CH2Cl2 / 4 h / Ambient temperature
7: 1.) LDA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to -20 deg C, 1.5 h
With
pyridine; hydrogenchloride; n-butyllithium; 3 A molecular sieve; sulfuric acid; hydrogen bromide; iron(III) chloride; pyrographite; hydrazine hydrate; pyridinium chlorochromate; potassium iodide; copper(I) bromide; lithium diisopropyl amide; sodium nitrite;
In
methanol; dichloromethane;
DOI:10.1021/jo00383a032