2-(4-iodophenyl)ethanol

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

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

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

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

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

Procedure: To a 500 mL round-bottomed flask equipped with dropping funnel, condenser and N2 inlet were added 307 g (124 mmol) 2-(4-iodophenyl)ethanol, 200 mL chloroform, and 10.0 mL (124 mmol) pyrdine. A solution of 13.5 mL (186 mmol) thionyl chloride in 50 mL chloroform was added dropwise over 15 min, and the reaction then heated at reflux for 2 hr. The reaction was cooled, the solvent evaporated, and the residue taken up in ethyl acetate, washed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine, dried, and evaporated. The resulting oil was chromatographed on silica gel using 20% ethyl acetate in hexane as eluant to afford 32.6 g (99%) of the product as an oil. To a 500 mL round-bottomed flask equipped the reaction then heated at reflux for 2 hr The reaction was cooled the solvent evaporated washed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine dried evaporated The resulting oil was chromatographed on silica gel using 20% ethyl acetate in hexane as eluant

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

Procedure: To a 500 mL round-bottomed flask equipped with dropping funnel, condenser and N2 inlet were added 307 g (124 mmol) 2-(4-iodophenyl)ethanol, 200 mL chloroform, and 10.0 mL (124 mmol) pyrdine. A solution of 13.5 mL (186 mmol) thionyl chloride in 50 mL chloroform was added dropwise over 15 min, and the reaction then heated at reflux for 2 hr. The reaction was cooled, the solvent evaporated, and the residue taken up in ethyl acetate, washed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine, dried, and evaporated. The resulting oil was chromatographed on silica gel using 20% ethyl acetate in hexane as eluant to afford 32.6 g (99%) of the product as an oil. To a 500 mL round-bottomed flask equipped the reaction then heated at reflux for 2 hr The reaction was cooled the solvent evaporated washed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine dried evaporated The resulting oil was chromatographed on silica gel using 20% ethyl acetate in hexane as eluant

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

Procedure: The title compound was prepared according to the procedure described in step 1 Example 45 from 4-methyl-2-nitroaniline and 4-iodophenylethyl alcohol.

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

Procedure: Prepared analogously to Example 1.2.b. from 2-(4-iodophenyl)ethanol and methanesulfonic acid chloride. Yield: 5.7 g (77.4% of theory); C9H11IO3S (M=326.15); calc.: molecular ion peak (M)+: 326; found: molecular ion peak (M)+: 326. Prepared analogously to Example 1.2.b

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

Procedure: 0.474 g (2.48 mmol) of copper (I) iodide, 5 g (24.86 mmol 2-(4-bromophenyl)ethanol and 7.45 g (49.73 mmol) of sodium iodide are successively added to a flask under an argon atmosphere. Then 0.438 g (4.97 mmol) of dimethylenediamine and 25 mL dioxane are added and the reaction mixture is refluxed for 14 hours. Then the reaction mixture is combined with 20 mL concentrated ammonia solution at ambient temperature, with 100 mL of water diluted and extracted with dichloromethane. The organic phase is extracted three times with water and dried over sodium sulfate. Yield: 5.4 g (87.5% of theory); C8H9IO (M=248.06); calc.: molecular ion peak (M)+: 248; found: molecular ion peak (M)+: 248; Rf value: 0.6 (silica gel, dichloromethane/ethanol (10:1)). the reaction mixture is refluxed for 14 hours diluted extracted with dichloromethane The organic phase is extracted three times with water dried over sodium sulfate

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

Procedure: 0.474 g (2.48 mmol) of copper (I) iodide, 5 g (24.86 mmol 2-(4-bromophenyl)ethanol and 7.45 g (49.73 mmol) of sodium iodide are successively added to a flask under an argon atmosphere. Then 0.438 g (4.97 mmol) of dimethylenediamine and 25 mL dioxane are added and the reaction mixture is refluxed for 14 hours. Then the reaction mixture is combined with 20 mL concentrated ammonia solution at ambient temperature, with 100 mL of water diluted and extracted with dichloromethane. The organic phase is extracted three times with water and dried over sodium sulfate. Yield: 5.4 g (87.5% of theory); C8H9IO (M=248.06); calc.: molecular ion peak (M)+: 248; found: molecular ion peak (M)+: 248; Rf value: 0.6 (silica gel, dichloromethane/ethanol (10:1)). the reaction mixture is refluxed for 14 hours diluted extracted with dichloromethane The organic phase is extracted three times with water dried over sodium sulfate

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

Procedure: The product was prepared analogously to Example 48.1c from 1.74 g (8.06 mmol) of 5-(4-chlorophenyl)-2-ethynylpyridine and 2.00 g (8.06 mmol) of 2-(4-iodophenyl)ethanol (24 at RT, triethylamine as base and acetonitrile as solvent). Yield: 1.80 g (67% of theoretical); C21H16ClNO (M=333.811); calc.: molpeak (M+H)+:334/336 (Cl); found: molpeak (M+H)+:334/336 (Cl).

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

Procedure: The title compound was prepared according to the procedure described in step 1 Example 45 from 4-methyl-2-nitroaniline and 4-iodophenylethyl alcohol.