phenyllithium in tetrahydrofuran T=-78°C; 0.5 h;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethanol; toluene 6 h; Heating;

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1: TsOH / ethanol 2: (i) nBuLi, Me2NCH2CH2NMe2, (ii) /BRN= 1209232/ 3: NBS / CCl4 / Irradiation View Scheme

1: 93 percent / 30percent aq. H2O2 / acetic acid / 3 h / Ambient temperature 2: 1) LDA / 1) THF, -78 deg C, 3 h, 2) -78 deg C, 3 h 3: 47 percent / tetrahydrofuran / 0.5 h / -78 °C 4: 99 percent / PhLi / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: 65 percent / PhLi / tetrahydrofuran / 12 h / Heating 2: 93 percent / 30percent aq. H2O2 / acetic acid / 3 h / Ambient temperature 3: 1) LDA / 1) THF, -78 deg C, 3 h, 2) -78 deg C, 3 h 4: 47 percent / tetrahydrofuran / 0.5 h / -78 °C 5: 99 percent / PhLi / tetrahydrofuran / 0.5 h / -78 °C View Scheme

sodium

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