1: benzyl alcohol With sodium hydride in tetrahydrofuran 1 h; 2: 1-bromo-3,5-difluoro-benzene in tetrahydrofuran T=20°C; 49 h;

copper(l) iodide; 1,10-phenanthroline; caesium carbonate in 1,4-dioxane T=110°C; 48 h;

dimethylammonium 2,4-dichlorophenoxyacetate; benzyl alcohol; dibenzoyl peroxide in tetrachloromethane; mineral oil

1: With AlCl3, aluminium chloride; N,N-dimethyl-aniline in dichloromethane T=0°C; 2.16667 h; 2: With hydrogenchloride in dichloromethane; water 3: With hydrogenchloride; potassium hydroxide more than 3 stages;

n-butyllithium; benzyl alcohol in hexane; isobutyramide; Petroleum ether

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 66 percent / tetrahydrofuran; hexane / -78 - 4 °C 2.1: 67 percent / NaH / dimethylformamide / 3 h / 20 °C 3.1: 94 percent / H2 / Pd(OH)2/C / ethanol / 15 h / 20 °C / atmospheric pressure View Scheme

1: 34 percent / NaH; CuBr / dioxane / Heating 2: 57 percent / aq. LiOH / dimethylsulfoxide / Heating 3: 58 percent / NaH; NaI; 15-crown-15 / dimethylformamide / 20 °C 4: 100 percent / H2 / Pd/C / ethanol / 20 °C 5: 61 percent / K2CO3 / dimethylformamide / 120 °C 6: 96 percent / aq. LiOH / methanol; tetrahydrofuran / Heating 7: (COCl)2 / CH2Cl2 / 0 - 20 °C 8: NH3 / CH2Cl2 / 20 °C View Scheme