Multi-step reaction with 12 steps
1: 53 percent / K2CO3 / acetone / 192 h / 25 °C
2: 56 percent / Br2 / CHCl3 / 25 °C
3: 1.) NaH / 1.) THF, 30 min, 1.5 h, 2.) from -5 to 25 deg C
5: 81 percent / 2 N aq. Na2CO3, Pd(PPh3)4 / benzene; ethanol / 42 h / Heating
6: 95 percent / conc. HCl / CHCl3; ethanol / 24 h / Ambient temperature
7: 1) hexamethylenetetraamine, 2.) H2O / 1.) 85-90 deg C, 36 h, 2.) 60 deg C, 3 h
8: 45 percent / Cs2CO3 / dimethylformamide / 3 h / 50 °C
9: p-toluenesulfonic acid monohydrate / toluene / 36 h / Heating
10: 90 percent / 3 N HCl / aq. ethanol / 2 h / Heating
11: 92 percent / NaBH4 / ethanol / 12 h
12: 83 percent / PBr3 / benzene / 3 h / 25 °C
With
hydrogenchloride; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); hexamethylenetetramine; water; bromine; phosphorus tribromide; sodium hydride; sodium carbonate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid;
In
ethanol; chloroform; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/jo00284a018