Multi-step reaction with 6 steps
1: 55 percent / phosphorus tribromide, pyridine / diethyl ether / 1 h / 0 °C
2: 1.) n-butyllithium, TMEDA / 1.) ether, -78 deg C, 2.) ether, from -78 deg C to RT, 7.5 h
3: 78.7 percent / CCl4, triphenylphosphine / 1 h / Heating
4: 1.) n-butyllithium, TMEDA / 1.) ether, 0 deg C, 2.) ether, from -78 deg C to RT, overnight
5: 82 percent / DMAP, pyridine / CH2Cl2 / 4.17 h / 0 - 20 °C
6: 76 percent / Pd2(dba)3*CHCl3, triphenylphosphine / tetrahydrofuran / 50 °C
With
pyridine; tetrachloromethane; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; phosphorus tribromide; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00074a008