Multi-step reaction with 9 steps
1: 1.) NaNO2, HBr, 2.) CuBr
2: 1.) tetrakis(triphenylphosphine)palladium(0), 2.) sodium carbonate / 1.) 1,2-dimethoxyethane, 20 min, 2.) 1,2-dimethoxyethane, water, reflux
3: 97 percent / hydrogen / Pd/C / ethanol
5: 87 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1 h / Heating
6: 77 percent / dimethylformamide / Ambient temperature
7: 100 percent / hydrazine hydrate / methanol / Heating
8: 75 percent / sodium carbonate / CH2Cl2 / Ambient temperature
9: 1.) thionyl chloride, 2.) potassium tert-butoxide / 1.) ether, reflux, 2.) THF, 0 -> 20 deg C
With
N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); thionyl chloride; Perbenzoic acid; potassium tert-butylate; hydrogen bromide; hydrogen; sodium carbonate; hydrazine hydrate; copper(I) bromide; sodium nitrite;
palladium on activated charcoal;
In
methanol; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;