Multi-step reaction with 6 steps
1: 73 percent / HIO4*2H2O, I2, H2SO4 / aq. acetic acid / 4 h / 80 °C
2: 94 percent / 48percent HBr, Br2, aq. NaNO2 / 0.5 h / 0 °C
3: 77 percent / NaH / dimethylformamide / 1.) 0 deg C to r.t., 3 h, 2.) 75 deg C, 16 h
4: tri-n-butylamine / Pd(dba)2, 1,3-bis(diphenylphosphino)propane / acetonitrile / 1.) r.t., 20 min, 2.) 80 deg C, 8 h
5: 82 percent / acetic acid, tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
6: 99 percent / sodium triacetoxyborohydride / acetonitrile; acetic acid / 0.17 h / 0 °C
With
tributyl-amine; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen bromide; bromine; iodine; sodium tris(acetoxy)borohydride; sodium hydride; acetic acid; periodic acid; sodium nitrite;
1,3-bis-(diphenylphosphino)propane; bis(dibenzylideneacetone)-palladium(0);
In
tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00121a071