(4-CHLOROPHENYLETHYNYL)TRIMETHYLSILANE

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Anhydrous potassium carbonate (0.9g, 0.0065 moles) was added to a solution of chloro-4-trimethylsilylethynylbenzene (3.Og, 0.014 moles) in methanol (60 cm3) under an atmosphere of nitrogen. The reaction was stirred, under nitrogen, at room temperature for 4 hours. The solvent was removed, the solid residue was tritura&ed with ether and then dichloromethane and filtered. The organic filtrates were combined and evaporated to dryness giving chloro-4-ethynylbenzene as a brown solid. This was used in the next step without any further purification yield 1.1 g (58%). 1H NMR 67.3 (2H, d), 7.4 (2H, d), 3.1 (1H, s)ppm. The solvent was removed dichloromethane and filtered evaporated to dryness

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

Procedure: Anhydrous potassium carbonate (0.9g, 0.0065 moles) was added to a solution of chloro-4-trimethylsilylethynylbenzene (3.Og, 0.014 moles) in methanol (60 cm3) under an atmosphere of nitrogen. The reaction was stirred, under nitrogen, at room temperature for 4 hours. The solvent was removed, the solid residue was tritura&ed with ether and then dichloromethane and filtered. The organic filtrates were combined and evaporated to dryness giving chloro-4-ethynylbenzene as a brown solid. This was used in the next step without any further purification yield 1.1 g (58%). 1H NMR 67.3 (2H, d), 7.4 (2H, d), 3.1 (1H, s)ppm. The solvent was removed dichloromethane and filtered evaporated to dryness

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

Procedure: Anhydrous potassium carbonate (0.9g, 0.0065 moles) was added to a solution of chloro-4-trimethylsilylethynylbenzene (3.Og, 0.014 moles) in methanol (60 cm3) under an atmosphere of nitrogen. The reaction was stirred, under nitrogen, at room temperature for 4 hours. The solvent was removed, the solid residue was tritura&ed with ether and then dichloromethane and filtered. The organic filtrates were combined and evaporated to dryness giving chloro-4-ethynylbenzene as a brown solid. This was used in the next step without any further purification yield 1.1 g (58%). 1H NMR 67.3 (2H, d), 7.4 (2H, d), 3.1 (1H, s)ppm. The solvent was removed dichloromethane and filtered evaporated to dryness

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 2(4-chlorophenyl)-1-trimethylsilylethyne Prepared in Stage 1 (30.90g:0.02 mole) in methanol was added potassium carbonate (0.276g:002 mole). The mixture was stirred at room temperature until starting material disappeared as monitored by gas liquid chromatography. After this time, solvent was removed in vacuo and the residue taken up in dichloromethane. The solution was dried and declourised over charcoal. Filtration, followed by removal of solvent gave a brown solid which was passed through silica in hexane. This gave pale yellow crystals (1.511g:55.3%) After this time, solvent was removed in vacuo The solution was dried Filtration followed by removal of solvent gave a brown solid which

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

Procedure: To a solution of 4-chloroiodobenzene (4.77 g:0.02 mole) in dry acetonitrile (30 ml) and triethylamine (2.02 g:0.02 mole) under nitrogen, was added copper iodide (0.2 g:1.05 mole), bis (triphenylphosphine)palladium dichloride (0.2 g=0.285 mmole) and trimethylsilylethyne (2.156 g:0.022 mole). The mixture was stirred for three hours during which time there was an exotherm at 20° C. and a darkening of the reacton mixture. The mixture was poured into saturated ammonium chloride solution (100 ml) and was extracted with ether (×3). The extracts were combined, washed with dilute hydrochloric acid and dried over magnesium sulfate and then filtered through charcoal. Removal of solvent in vacuo gave a brown oil which was titurated with hexane and filtered to remove by-products. The filtrate was evaporated to give yellow crystals (3.90 g). at 20° C. was extracted with ether (×3) washed with dilute hydrochloric acid dried over magnesium sulfate filtered through charcoal Removal of solvent in vacuo gave a brown oil which filtered to remove by-products The filtrate was evaporated

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

Procedure: Anhydrous potassium carbonate (0.9g, 0.0065 moles) was added to a solution of chloro-4-trimethylsilylethynylbenzene (3.Og, 0.014 moles) in methanol (60 cm3) under an atmosphere of nitrogen. The reaction was stirred, under nitrogen, at room temperature for 4 hours. The solvent was removed, the solid residue was tritura&ed with ether and then dichloromethane and filtered. The organic filtrates were combined and evaporated to dryness giving chloro-4-ethynylbenzene as a brown solid. This was used in the next step without any further purification yield 1.1 g (58%). 1H NMR 67.3 (2H, d), 7.4 (2H, d), 3.1 (1H, s)ppm. The solvent was removed dichloromethane and filtered evaporated to dryness