1: With copper(l) chloride in diethyl ether; toluene 2 h; Reflux; 2: With sulfuric acid; water in diethyl ether; toluene T=25°C; 2 h; Reflux; 3: With sodium carbonate in diethyl ether; water; toluene

potassium carbonate; sodium bromide in water; N,N-dimethyl-formamide T=70°C; 20 h;

potassium carbonate in butanone T=78 - 80°C;

sodium carbonate in N,N-dimethyl-formamide T=65 - 90°C; 14 h;

1: 1-bromo-3-chloro-propane; 4'-hydroxy-3'-methoxyacetophenone With tetrabutylammomium bromide; potassium carbonate in acetonitrile T=80°C; Industry scale; 2: 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole monohydrochloride With tetrabutylammomium bromide; potassium carbonate in methanol T=60 - 65°C; autoclave;

1: 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole monohydrochloride With sodium hydroxide in water T=25 - 30°C; 0.25 h; Industrial scaleGreen chemistry; 2: 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone in water T=25 - 30°C; 0.25 h; Industrial scaleGreen chemistry; 3: With tetrabutylammomium bromide in n-heptane; water T=65 - 70°C; Industrial scaleGreen chemistry; Reagent/catalystSolventTemperatureConcentrationTime;

triethylamine in methanol

in N-methyl-acetamide

in N,N-dimethyl-formamide T=90°C; 16.1667 h;

diisopropylamine in methanol Reflux;