Multi-step reaction with 6 steps
1: 55 percent / N-bromosuccinimide, (PhCO2)2 / CCl4 / 48 h / Heating
2: 76 percent / Li2CO3, LiBr / dimethylformamide / 6 h / 130 °C
3: 1) n-BuLi, 2) lithium 2-thienylcyanocuprate, 3) BF3*Et2O / 1) THF, hexane, a) 0 deg C, 10 min b) 25 deg C, 2,5 h, 2) -78 deg C, 3) THF, -78 deg C, 5-6 h
4: 65 percent / trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 60 h / 22 °C
5: 71 percent / 50percent aq. HClO4 / acetone / 48 h / 40 °C
6: Li-dimethyl cuprate / 1) ether, 0 deg C, 2) DME, 0 deg C, 5 h
With
N-Bromosuccinimide; n-butyllithium; perchloric acid; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; lithium dimethylcuprate; lithium carbonate; thien-2-yl(cyano)copper lithium; lithium bromide; dibenzoyl peroxide;
In
tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)85608-8