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1: With thionyl chloride; N,N-dimethyl-formamide T=20°C; 1 - 2 h; 2: With AlCl3, aluminium chloride T=0 - 5°C; 1 - 2 h;

aluminium trichloride in 1,2-dichloro-ethane T=20°C; Friedel-Crafts cyclization;

thionyl chloride; aluminium trichloride in methanol; water; N,N-dimethyl-formamide

1.1: 92 percent / TiCl4 / CH2Cl2 / 1 h 2.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 2.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 3.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 4.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 5.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 6.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 7.1: SOCl2 / 75 °C 8.1: AlCl3 / 1,2-dichloro-ethane / 20 °C View Scheme

1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 3.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 4.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 5.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 6.1: SOCl2 / 75 °C 7.1: AlCl3 / 1,2-dichloro-ethane / 20 °C View Scheme

1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 2: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 3: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 4: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 5: SOCl2 / 75 °C 6: AlCl3 / 1,2-dichloro-ethane / 20 °C View Scheme

1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 2: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 3: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 4: SOCl2 / 75 °C 5: AlCl3 / 1,2-dichloro-ethane / 20 °C View Scheme

1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 2: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 3: SOCl2 / 75 °C 4: AlCl3 / 1,2-dichloro-ethane / 20 °C View Scheme

1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 2: SOCl2 / 75 °C 3: AlCl3 / 1,2-dichloro-ethane / 20 °C View Scheme