1: With n-butyllithium in diethyl ether T=-65°C; 1.16667 h; Inert atmosphere; 2: With boron triethoxide in diethyl ether T=-65°C; 1 h; Inert atmosphere;

n-butyllithium in diethyl ether; hexane under Ar atm.; Et2O cooled to -65°C; n-BiLi in hexane added slowly to stirred solvent; bromide dropped; mixt. stirred for 1 h at -65°C; (EtO)3B dropped; mixt. stirred for 1 h at -65°C; H2SO4 quickly added; temp. rose until about 20; phases sepd.; aq. phase extd. (Et2O); solvent (about 3/4 vol.) removed (vac.); H2O added; evapd. for 0.5 h; aq. phase removed by decantation; hexane added; slurry kept at 4°C for 11 d; solid filtered off; dissolved (acetone/H2O); standing at room;

1: (methoxymethyleneoxy)phenol With n-butyllithium in tetrahydrofuran; hexane T=0°C; 2 h; 2: boric acid trimethyl ester in tetrahydrofuran; hexane 1 h; 3: With water; ammonium chloride in tetrahydrofuran; hexane 1 h;

1: 78 percent / PdCl2(PPh3)2, K2CO3 / various solvent(s) / 5 h / 80 °C 2: aq. HCl / methanol / 13 h / Ambient temperature 3: BF3*OEt2, MsCl / 21 h / 110 °C View Scheme

1: 78 percent / PdCl2(PPh3)2, K2CO3 / various solvent(s) / 5 h / 80 °C 2: aq. HCl / methanol / 13 h / Ambient temperature View Scheme

1: N,N-dimethyl-formamide / 3 h / 120 °C / |Inert atmosphere; |Molecular sieve 2: chloro-trimethyl-silane / acetonitrile; dichloromethane / 12 h / 20 °C / |Inert atmosphere 3: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; potassium phosphate / 1,4-dioxane; water / 12 h / 23 - 100 °C / |Inert atmosphere View Scheme