Multi-step reaction with 8 steps
1: t-BuOK / 2-methyl-propan-2-ol / 14 h / Heating
2: acetic acid, 48percent aq. HBr / 14 h / Heating
3: H2 / 10percent Pd/C / ethyl acetate / 2 h / 1551.4 Torr
4: SOCl2 / toluene / 1 h / Heating
5: 1.) AlCl3, 2.) hydroxylamine hydrochloride, Et3N / 1.) CS2, 16 h, 2.) MeOH, RT, 3 d
6: 51 percent / polyphosphoric acid / 0.42 h / 130 °C
7: 1.) PCl5, pyridine, 2.) Br2 / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, from -45 deg C to RT
8: 1.) LiN(SiMe3)2 / 1.) THF, 5 min, 2.) THF, DMSO, RT, 1 h
With
pyridine; aluminium trichloride; thionyl chloride; PPA; phosphorus pentachloride; hydroxylamine hydrochloride; potassium tert-butylate; hydrogen bromide; hydrogen; bromine; acetic acid; triethylamine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
ethyl acetate; toluene; tert-butyl alcohol;
DOI:10.1021/jm00048a015