potassium fluoride in methanol T=20°C; 3 h;

1: carbon tetrabromide With triphenylphosphine in dichloromethane T=0°C; 0.5 h; Inert atmosphere; 2: 2-(methoxymethyloxy)-benzaldehyde With triethylamine in dichloromethane T=0 - 20°C; Inert atmosphere; 3: With n-butyllithium in tetrahydrofuran; hexane T=-78 - 0°C; Inert atmosphere;

sodium hydroxide in toluene Heating;

1: 88 percent / triphenylphosphine; triethylamine; copper(I) iodide / bis(triphenylphosphine)palladium(II) chloride / 80 °C 2: 70 percent / sodium hydroxide / toluene / 3.5 h / Heating View Scheme

1: 99 percent / iPr2EtN / CH2Cl2 2: 88 percent / PPh3; Et3N; CuI / PdCl2(PPh3)2 3: 89 percent / sodium hydroxide / toluene / Heating View Scheme

1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / |Inert atmosphere 2.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C / |Inert atmosphere 2.2: 0 - 20 °C / |Inert atmosphere 2.3: -78 - 0 °C / |Inert atmosphere View Scheme

1.1: 85 percent / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran / 19 h / 50 °C 2.1: 93 percent / aq. HCl / methanol / 3 h / 20 °C 3.1: TMEDA; Et2Zn / toluene / 3 h / 120 °C 3.2: 93 percent / aq. NH4Cl / toluene View Scheme

1: 1-ethynyl-2-(methoxymethoxy)benzene With n-butyllithium in tetrahydrofuran; hexane T=-35°C; 0.333333 h; 2: chloroformic acid ethyl ester in tetrahydrofuran; hexane 0.5 h;