Multi-step reaction with 7 steps
1: 55 percent / n-BuLi, BrF2CH2CH2F2Br / toluene / -20 °C
2: 90 percent / NaBr, NaOCl, TEMPO / tetrahydrofuran / 3 h / 0 °C
3: 96 percent / p-TSA*H2O / toluene / 1.5 h / Heating
4: 79 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -60 deg C, 15 min, 2.) -65 deg C, 4 h; r.t., 16 h
5: 73 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 60 min, 2.) 0 deg C, 2 h; r.t., overnight
6: 93 percent / MnO2 / CH2Cl2 / 48 h / Ambient temperature
7: 88 percent / TBAF / tetrahydrofuran / 1.5 h / Ambient temperature
With
manganese(IV) oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; n-butyllithium; BrF2CH2CH2F2Br; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; sodium bromide;
In
tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo00101a032