1: With potassium carbonate in acetonitrile T=20°C; Substitution; 2: With potassium carbonate; p-toluenesulfonyl chloride in acetonitrile T=20°C; Chlorination;

1.1: 100 percent / CH3COOH / benzene / Heating 2.1: 64 percent / diphenyl ether / 250 °C 3.1: 99 percent / K2CO3 / dimethylformamide / 60 °C 4.1: 85 percent / m-chloroperoxybenzoic acid (MCPBA) / CHCl3 / 20 °C 5.1: K2CO3 / acetonitrile / 20 °C 5.2: 75 percent / K2CO3; TsCl / acetonitrile / 20 °C View Scheme

1.1: 99 percent / K2CO3 / dimethylformamide / 60 °C 2.1: 85 percent / m-chloroperoxybenzoic acid (MCPBA) / CHCl3 / 20 °C 3.1: K2CO3 / acetonitrile / 20 °C 3.2: 75 percent / K2CO3; TsCl / acetonitrile / 20 °C View Scheme

1.1: 99 percent / K2CO3 / dimethylformamide / 60 °C 2.1: 85 percent / m-chloroperoxybenzoic acid (MCPBA) / CHCl3 / 20 °C 3.1: K2CO3 / acetonitrile / 20 °C 3.2: 75 percent / K2CO3; TsCl / acetonitrile / 20 °C View Scheme

1.1: 100 percent / CH3COOH / benzene / Heating 2.1: 64 percent / diphenyl ether / 250 °C 3.1: 99 percent / K2CO3 / dimethylformamide / 60 °C 4.1: 85 percent / m-chloroperoxybenzoic acid (MCPBA) / CHCl3 / 20 °C 5.1: K2CO3 / acetonitrile / 20 °C 5.2: 75 percent / K2CO3; TsCl / acetonitrile / 20 °C View Scheme

1.1: 64 percent / diphenyl ether / 250 °C 2.1: 99 percent / K2CO3 / dimethylformamide / 60 °C 3.1: 85 percent / m-chloroperoxybenzoic acid (MCPBA) / CHCl3 / 20 °C 4.1: K2CO3 / acetonitrile / 20 °C 4.2: 75 percent / K2CO3; TsCl / acetonitrile / 20 °C View Scheme

1.1: 85 percent / m-chloroperoxybenzoic acid (MCPBA) / CHCl3 / 20 °C 2.1: K2CO3 / acetonitrile / 20 °C 2.2: 75 percent / K2CO3; TsCl / acetonitrile / 20 °C View Scheme