tert-butyl-(4-iodophenoxy)-dimethylsilane

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

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

Procedure: 387 mg of irdidazole and 411 mg of tertbutyldimethylsilyl chloride is added at ambient temperature and under an inert atmosphere to 500 mg of para-iodo-phenol in 4 ml of dimethylformamide and the mixture is maintained under agitation for 15 hours at ambient temperature then for 1 hour at 40° C. The reaction medium is poured into water, and the aqueous phase is extracted with dichloromethane. The organic phase is then dried and evaporated under reduced pressure. In this way 636 mg of expected product is obtained. the aqueous phase is extracted with dichloromethane The organic phase is then dried evaporated under reduced pressure

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

Procedure: 4-Iodophenol (1.0 g, 4.55 mmol) was dissolved in dichloromethane (5 mL). tert-Butyldimethylsilyl chloride (0.685 g, 4.55 mmol) and imidazole (0.309 g, 4.55 mmol) were added. The reaction was stirred overnight at room temperature. The reaction mixture was partitioned between water (30 mL) and dichloromethane (30 mL). The organic layer was removed and the aqueous layer was extracted with dichloromethane (30 mL). The organic layers were combined, dried and concentrated, and the residue was purified by chromatography (0-10% EtOAc/hexanes) to give the title compound as a light yellow oil (1.45 g, 94%). The reaction mixture was partitioned between water (30 mL) and dichloromethane (30 mL) The organic layer was removed the aqueous layer was extracted with dichloromethane (30 mL) dried concentrated the residue was purified by chromatography (0-10% EtOAc/hexanes)

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

Procedure: 387 mg of imidazole and 411 mg of tertbutyldimethylsilyl chloride is added at ambient temperature and under an inert atmosphere to 500 mg of para-iodo-phenol in 4 ml of dimethylformamide and the mixture is maintained under agitation for 15 hours at ambient temperature then for 1 hour at 40° C. The reaction medium is poured into water, and the aqueous phase is extracted with dichloromethane. The organic phase is then dried and evaporated under reduced pressure. In this way 636 mg of expected product is obtained. the aqueous phase is extracted with dichloromethane The organic phase is then dried evaporated under reduced pressure

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

Procedure: 387 mg of imidazole and 411 mg of tertbutyldimethylsilyl chloride is added at ambient temperature and under an inert atmosphere to 500 mg of para-iodo-phenol in 4 ml of dimethylformamide and the mixture is maintained under agitation for 15 hours at ambient temperature then for 1 hour at 40° C. The reaction medium is poured into water, and the aqueous phase is extracted with dichloromethane. The organic phase is then dried and evaporated under reduced pressure. In this way 636 mg of expected product is obtained. the aqueous phase is extracted with dichloromethane The organic phase is then dried evaporated under reduced pressure

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

Procedure: A mixture of 3.00 g (24.4 mmol) 1-but-3-enyl-1H-[1,2,3]triazole, 6.79 g (20.3 mmol) tert-butyl-(4-iodo-phenoxy)-dimethyl-silane, 1.07 g (4.06 mmol) triphenylphosphine, 0.685 g (3.05 mmol) palladium(II)acetate and 56 ml triethylamine was heated to reflux for 24 h. The reaction mixture was cooled to r.t., evaporated, stirred with ice and adjusted to pH=1 by addition of conc. HCl. The organic material was collected with ethyl acetate/dichloromethane 1:2, the organic phase dried over sodium sulfate and evaporated. The residue was stirred with 20.3 ml 1M solution of tetrabutylammonium fluoride solution in THF at 28° C. for 3 h. After removal of THF, the residue was dissolved in dichloromethane, washed with water, evaporated and purified by chromatography on silica gel (ethyl acetate/n-heptane 5:1). The product containing fractions were collected, evaporated and stirred with little ethyl acetate/n-heptane 3:1 to yield 1.53 g (29%). was heated to reflux for 24 h evaporated adjusted to pH=1 by addition of conc. HCl The organic material was collected with ethyl acetate/dichloromethane 1:2 the organic phase dried over sodium sulfate evaporated The residue was stirred with 20.3 ml 1M solution of tetrabutylammonium fluoride solution in THF at 28° C. for 3 h After removal of THF the residue was dissolved in dichloromethane washed with water evaporated purified by chromatography on silica gel (ethyl acetate/n-heptane 5:1) The product containing fractions were collected evaporated stirred with little ethyl acetate/n-heptane 3:1 to yield 1.53 g (29%)

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

Procedure: 387 mg of irdidazole and 411 mg of tertbutyldimethylsilyl chloride is added at ambient temperature and under an inert atmosphere to 500 mg of para-iodo-phenol in 4 ml of dimethylformamide and the mixture is maintained under agitation for 15 hours at ambient temperature then for 1 hour at 40° C. The reaction medium is poured into water, and the aqueous phase is extracted with dichloromethane. The organic phase is then dried and evaporated under reduced pressure. In this way 636 mg of expected product is obtained. the aqueous phase is extracted with dichloromethane The organic phase is then dried evaporated under reduced pressure

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

Procedure: 4-Iodophenol (1.0 g, 4.55 mmol) was dissolved in dichloromethane (5 mL). tert-Butyldimethylsilyl chloride (0.685 g, 4.55 mmol) and imidazole (0.309 g, 4.55 mmol) were added. The reaction was stirred overnight at room temperature. The reaction mixture was partitioned between water (30 mL) and dichloromethane (30 mL). The organic layer was removed and the aqueous layer was extracted with dichloromethane (30 mL). The organic layers were combined, dried and concentrated, and the residue was purified by chromatography (0-10% EtOAc/hexanes) to give the title compound as a light yellow oil (1.45 g, 94%). The reaction mixture was partitioned between water (30 mL) and dichloromethane (30 mL) The organic layer was removed the aqueous layer was extracted with dichloromethane (30 mL) dried concentrated the residue was purified by chromatography (0-10% EtOAc/hexanes)

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

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

Procedure: A solution of t-butyl-dimethylsilyl chloride (3.0 g) in dichloromethane (10 ml) was added dropwise to a stirred solution of 4-iodophenol (4.4 g) and imidazole (1.4 g) in dichloromethane (90 ml) whilst maintaining the temperature between 10° C. and 5° C. After the addition was complete, the reaction mixture was stirred for a further 4 hours at ambient temperature. The reaction mixture was washed with water, dried (MgSO4), and evaporated to give 4-(t-butyldimethylsilyloxy)iodobenzene as a colourless oil (6.4 g) NMR(DMSO-d6): 0.0(6H,s), 0.8(9H,s), 6.49-6.58(2H,d), 7.35-7.44(2H,d); m/z=334 (M). whilst maintaining the temperature between 10° C. and 5° C After the addition The reaction mixture was washed with water dried (MgSO4) evaporated

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

Procedure: A solution of t-butyl-dimethylsilyl chloride (3.0 g) in dichloromethane (10 ml) was added dropwise to a stirred solution of 4-iodophenol (4.4 g) and imidazole (1.4 g) in dichloromethane (90 ml) whilst maintaining the temperature between 10° C. and 5° C. After the addition was complete, the reaction mixture was stirred for a further 4 hours at ambient temperature. The reaction mixture was washed with water, dried (MgSO4), and evaporated to give 4-(t-butyldimethylsilyloxy)iodobenzene as a colourless oil (6.4 g) NMR(DMSO-d6): 0.0(6H,s), 0.8(9H,s), 6.49-6.58(2H,d), 7.35-7.44(2H,d); m/z=334 (M). whilst maintaining the temperature between 10° C. and 5° C After the addition The reaction mixture was washed with water dried (MgSO4) evaporated

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

Procedure: A solution of t-butyl-dimethylsilyl chloride (3.0 g) in dichloromethane (10 ml) was added dropwise to a stirred solution of 4-iodophenol (4.4 g) and imidazole (1.4 g) in dichloromethane (90 ml) whilst maintaining the temperature between 10° C. and 5° C. After the addition was complete, the reaction mixture was stirred for a further 4 hours at ambient temperature. The reaction mixture was washed with water, dried (MgSO4), and evaporated to give 4-(t-butyldimethylsilyloxy)iodobenzene as a colourless oil (6.4 g) NMR(DMSO-d6): 0.0(6H,s), 0.8(9H,s), 6.49-6.58(2H,d), 7.35-7.44(2H,d); m/z=334 (M). whilst maintaining the temperature between 10° C. and 5° C After the addition The reaction mixture was washed with water dried (MgSO4) evaporated