sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl in 1,4-dioxane 0.25 h; Heating / reflux;

N-ethyl-N,N-diisopropylamine in toluene T=110°C; 20 h;

N-hexadecyl-N,N,N-trimethylammonium bromide in water T=0°C; bromination at various temperature; Product distribution;

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 80 °C 2: potassium carbonate / methanol / 12 h / 20 °C 3: 4-methylmorpholine N-oxide; trifluoroacetic acid / dichloromethane / 3 h / 30 °C View Scheme

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 80 °C 2: potassium carbonate / methanol / 12 h / 20 °C 3: methanesulfonic acid; 8-methylquinoline 1-oxide / dichloromethane / 3 h / 30 °C View Scheme

Yield given. Multistep reaction;