4-(4-fluorophenyl)-2-methylbut-3-yn-2-ol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 25.2 g (0.1 mole) of 1-4-(bromophenoxy)-2-diethylaminoethane and 17.8 g (0.1 mole) of 1-fluoro-4-(3-hydroxy-3-methyl-1-butyn-1-yl)benzene in 250 ml of triethylamine are added, under nitrogen, 11.2 g of pulverised potassium hydroxide, 0.7 g of the palladium complex PdCl2 [P(C6H5)3 ]2 and 0.13 g of copper(I) iodide. The reaction mixture is subsequently stirred for 14 hours at 80° C. The reaction mixture is taken up in 250 ml of ether and the solution is washed twice with 100 ml of water and 100 ml of aqueous K2CO3 solution, treated with activated charcoal and evaporated to dryness. Vacuum distillation of the residue yields 9.5 g (33%) of 1-[4-(4-fluorophenylethynyl)phenoxy]-2-diethylaminoethane with a boiling point of 156°-162° C./0.08 mb. the solution is washed twice with 100 ml of water and 100 ml of aqueous K2CO3 solution treated with activated charcoal evaporated to dryness Vacuum distillation of the residue

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 35.2 g (0.19 mole) of 4-bromofluorobenzene and 25.2 g (0.3 mole) of 3-hydroxy-3-methyl-1-butine in 250 ml of triethylamine are added, under nitrogen, 1 g of the palladium complex PdCl2 [P(C6H5)3 ]2 and 0.2 g of copper(I) iodide. The reaction mixture is subsequently stirred for 24 hours at 70° C. After filtering off triethylammonium bromide and removing excess triethylamine by evaporation, the residue is taken up in 200 ml of ether and the solution is washed twice with 100 ml of 5% aqueous HCl solution and 100 ml of water, dried, treated with activated charcoal, and evaporated to dryness. The residue is chromatographed on silica gel with a 1:1 mixture of ether/hexane, affording 26.4 g (78%) of 1-fluoro-4-(3-hydroxy-3-methyl-1-butyn-1-yl)-benzene with a melting point of 124° C. After filtering off triethylammonium bromide removing excess triethylamine by evaporation the solution is washed twice with 100 ml of 5% aqueous HCl solution and 100 ml of water dried treated with activated charcoal evaporated to dryness The residue is chromatographed on silica gel with a 1:1 mixture of ether/hexane