Multi-step reaction with 8 steps
1: 71 percent / hydroxylamine-O-sulfonic acid, formic acid / 1 h / Heating
2: 1.) t-BuOK / 1.) THF, RT, 10 min, 2.) THF, reflux, 1 h
3: 95 percent / Lawesson's reagent / hexamethylphosphoric acid triamide / 2.5 h / 100 °C
5: 2.) triethylamine / 1.) 65-70 deg C, 3 h, 2.) dichloromethane, RT, 1 h
6: 98 percent / Raney nickel W2 / acetone / 4 h / Heating
7: 1.) bromine, 2.) water, triethylamine / 1.) ether, dichloromethane, -70 deg C, 1.5 h, 2.) RT, 2 h
8: 59 percent / toluene / 40 h / 110 °C
With
Lawessons reagent; formic acid; potassium tert-butylate; water; bromine; triethylamine; hydroxylamine-O-sulfonic acid;
Raney nickel W2;
In
N,N,N,N,N,N-hexamethylphosphoric triamide; acetone; toluene;
DOI:10.1021/jo00279a034