1: methyl 3-methyl-4-iodobenzoate With isopropylmagnesium chloride in tetrahydrofuran T=-20°C; 2 h; 2: 2,7-difluoro-3,6-bis(2-methoxyethoxymethoxy)xanthen-9-one in tetrahydrofuran T=-20 - 22°C; 16 h; 3: With trifluoroacetic acid in dichloromethane T=22°C; 2 h;

toluene-4-sulfonic acid in toluene T=111°C; 24 h;

1.1: 92 percent / methanol 2.1: 91 percent / H2 / Pd/C / ethanol 3.1: 68 percent / HCl; NaNO2; NaI / H2O / 16 h / 0 - 22 °C 4.1: 96 percent / acetonitrile / 0.01 h / microwave irradiation 5.1: 72 percent / BBr3 / CH2Cl2 / 40 °C 6.1: 82 percent / 220 °C 7.1: 65 percent / NaH / dimethylformamide 8.1: iPrMgCl / tetrahydrofuran / 2 h / -20 °C 8.2: tetrahydrofuran / 16 h / -20 - 22 °C 8.3: 72 percent / TFA / CH2Cl2 / 2 h / 22 °C View Scheme

1.1: 91 percent / H2 / Pd/C / ethanol 2.1: 68 percent / HCl; NaNO2; NaI / H2O / 16 h / 0 - 22 °C 3.1: 96 percent / acetonitrile / 0.01 h / microwave irradiation 4.1: 72 percent / BBr3 / CH2Cl2 / 40 °C 5.1: 82 percent / 220 °C 6.1: 65 percent / NaH / dimethylformamide 7.1: iPrMgCl / tetrahydrofuran / 2 h / -20 °C 7.2: tetrahydrofuran / 16 h / -20 - 22 °C 7.3: 72 percent / TFA / CH2Cl2 / 2 h / 22 °C View Scheme

1: 88 percent / methanesulfonic acid / CH2Cl2; diethyl ether / 6 h / 23 °C 2: p-TsOH / toluene / 24 h / 111 °C View Scheme

1.1: i-PrMgCl / tetrahydrofuran; hexane / 2 h / -15 °C 1.2: 95 percent / tetrahydrofuran; hexane / 1 h / -15 - 23 °C 2.1: 88 percent / methanesulfonic acid / CH2Cl2; diethyl ether / 6 h / 23 °C 3.1: p-TsOH / toluene / 24 h / 111 °C View Scheme

1: 88 percent / methanesulfonic acid / CH2Cl2; diethyl ether / 6 h / 23 °C 2: p-TsOH / toluene / 24 h / 111 °C View Scheme

1.1: 96 percent / acetonitrile / 0.01 h / microwave irradiation 2.1: 72 percent / BBr3 / CH2Cl2 / 40 °C 3.1: 82 percent / 220 °C 4.1: 65 percent / NaH / dimethylformamide 5.1: iPrMgCl / tetrahydrofuran / 2 h / -20 °C 5.2: tetrahydrofuran / 16 h / -20 - 22 °C 5.3: 72 percent / TFA / CH2Cl2 / 2 h / 22 °C View Scheme

1.1: 68 percent / HCl; NaNO2; NaI / H2O / 16 h / 0 - 22 °C 2.1: 96 percent / acetonitrile / 0.01 h / microwave irradiation 3.1: 72 percent / BBr3 / CH2Cl2 / 40 °C 4.1: 82 percent / 220 °C 5.1: 65 percent / NaH / dimethylformamide 6.1: iPrMgCl / tetrahydrofuran / 2 h / -20 °C 6.2: tetrahydrofuran / 16 h / -20 - 22 °C 6.3: 72 percent / TFA / CH2Cl2 / 2 h / 22 °C View Scheme

1.1: 65 percent / NaH / dimethylformamide 2.1: iPrMgCl / tetrahydrofuran / 2 h / -20 °C 2.2: tetrahydrofuran / 16 h / -20 - 22 °C 2.3: 72 percent / TFA / CH2Cl2 / 2 h / 22 °C View Scheme