Multi-step reaction with 6 steps
1: 86 percent / 2,4,4,6-tetrabromo-cyclohexa-2,5-dienone / diethyl ether / 0 °C
2: 70 percent / Et3N / diethyl ether / 1 h / 0 °C
3: 93 percent / PBr3 / diethyl ether; CH2Cl2 / 1.) 25 deg C, 5 min, 2.) reflux, 30 min
4: 63 percent / KOtBu / tetrahydrofuran / 0.75 h / 5 °C
5: 63 percent / Mg / 1.5 h / 25 °C
6: 1.) LiN(SiMe3)2, NaI / 1.) THF/DMF, -70 deg C, 5 min, -10 deg C, 10 min, 2.) THF/DMF, 2.5 h, -10 deg C
With
2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; potassium tert-butylate; phosphorus tribromide; magnesium; triethylamine; sodium iodide; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/0040-4039(96)01573-0