Multi-step reaction with 12 steps
1: 85 percent / K2CO3 / dimethylformamide / 3.3 h / 55 °C
2: 82 percent / thallium trinitrate; aq. perchloric acid / methanol / 4.3 h / 20 °C
3: 99 percent / NBS; SiO2 (Micro Bead 3 Angstroem) / CHCl3 / 1.17 h / 20 °C
4: 78 percent / aq. NaOH / methanol / 3.5 h / 20 °C
5: (COCl)2 / 2.5 h / 20 °C
6: 0.707 g / SnCl4 / CH2Cl2 / 1.08 h / -78 °C
7: 71 percent / conc. H2SO4; AcOH / 4 h / 50 °C
8: 33 percent / pyridine / 7.5 h / 120 °C
9: 86 percent / 0.5 h / 250 °C
10: 97 percent / AIBN; tributyltin hydride / toluene / 5.5 h / 115 - 140 °C
11: 64 percent / SnCl4 / CH2Cl2 / 4.5 h / -40 - -25 °C
12: 88 percent / aq. HCOOH; aq. H2O2 / 4 h / 0 °C
With
pyridine; sodium hydroxide; N-Bromosuccinimide; formic acid; perchloric acid; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); SiO2 (Micro Bead 3 Angstroem); sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; tin(IV) chloride; potassium carbonate; acetic acid; thallium(III) nitrate;
In
methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
6: Friedel-Crafts acylation / 11: Friedel-Crafts acylation / 12: Baeyer-Villiger oxidation;
DOI:10.3987/com-04-10060