[2-(2,4-dichlorophenoxy)phenyl]methanol

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

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

Procedure: Phosphorus(III) tribromide (0.41 ml, 4.37 mmol) was added to a solution of 1-[2-(2,4-dichlorophenoxy)phenyl]methanol (420 mg, 1.56 mmol) in dioxane (10 ml). The reaction mixture was stirred for 1 hour at room temperature. Another portion of phosphorus(III) tribromide (0.41 ml, 4.37 mmol) was added. The reaction mixture was stirred for 16 hours at room temperature. It was cooled to 0° C. Water (5 ml) was added dropwise. The reaction mixture was warmed to room temperature and diluted with ethyl acetate (400 ml). It was washed with a 10% aqueous solution of sodium hydrogensulphate. The aqueous phase was extracted with ethyl acetate (50 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (100 g), using ethyl acetate/heptane 1:3 as eluent, to give 297 mg of 2-(2,4-dichlorophenoxy)benzyl bromide. The reaction mixture was stirred for 16 hours at room temperature It was cooled to 0° C The reaction mixture was warmed to room temperature It was washed with a 10% aqueous solution of sodium hydrogensulphate The aqueous phase was extracted with ethyl acetate (50 ml) The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) dried over magnesium sulphate The solvent was removed in vacuo The crude product was purified by flash chromatography on silica (100 g)

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

Procedure: Sodium borohydride (119 mg, 3.15 mmol) was added to a solution of 2-(2,4-dichlorophenoxy)benzaldehyde (600 mg, 2.25 mmol) in isopropanol (10 ml) and DCM (20 ml). The reaction mixture was stirred for 2 hours at room temperature. A 10% aqueous solution of sodium hydrogensulphate (200 ml) was added dropwise. Ethyl acetate (300 ml) was added successively. The phases were separated. The aqueous phase was extracted with ethyl acetate (100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (100 g), using ethyl acetate/heptane 1:3 as eluent, to give 440 mg of 1-[2-(2,4-dichlorophenoxy)phenyl]methanol. The phases were separated The aqueous phase was extracted with ethyl acetate (100 ml) The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) dried over magnesium sulphate The solvent was removed in vacuo The crude product was purified by flash chromatography on silica (100 g)

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

Procedure: Phosphorus(III) tribromide (0.41 ml, 4.37 mmol) was added to a solution of 1-[2-(2,4-dichlorophenoxy)phenyl]methanol (420 mg, 1.56 mmol) in dioxane (10 ml). The reaction mixture was stirred for 1 hour at room temperature. Another portion of phosphorus(III) tribromide (0.41 ml, 4.37 mmol) was added. The reaction mixture was stirred for 16 hours at room temperature. It was cooled to 0° C. Water (5 ml) was added dropwise. The reaction mixture was warmed to room temperature and diluted with ethyl acetate (400 ml). It was washed with a 10% aqueous solution of sodium hydrogensulphate. The aqueous phase was extracted with ethyl acetate (50 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (100 g), using ethyl acetate/heptane 1:3 as eluent, to give 297 mg of 2-(2,4-dichlorophenoxy)benzyl bromide. The reaction mixture was stirred for 16 hours at room temperature It was cooled to 0° C The reaction mixture was warmed to room temperature It was washed with a 10% aqueous solution of sodium hydrogensulphate The aqueous phase was extracted with ethyl acetate (50 ml) The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) dried over magnesium sulphate The solvent was removed in vacuo The crude product was purified by flash chromatography on silica (100 g)

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

Procedure: Sodium borohydride (119 mg, 3.15 mmol) was added to a solution of 2-(2,4-dichlorophenoxy)benzaldehyde (600 mg, 2.25 mmol) in isopropanol (10 ml) and DCM (20 ml). The reaction mixture was stirred for 2 hours at room temperature. A 10% aqueous solution of sodium hydrogensulphate (200 ml) was added dropwise. Ethyl acetate (300 ml) was added successively. The phases were separated. The aqueous phase was extracted with ethyl acetate (100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (100 g), using ethyl acetate/heptane 1:3 as eluent, to give 440 mg of 1-[2-(2,4-dichlorophenoxy)phenyl]methanol. The phases were separated The aqueous phase was extracted with ethyl acetate (100 ml) The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) dried over magnesium sulphate The solvent was removed in vacuo The crude product was purified by flash chromatography on silica (100 g)

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

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

Procedure: Phosphorus(III) tribromide (0.41 ml, 4.37 mmol) was added to a solution of 1-[2-(2,4-dichlorophenoxy)phenyl]methanol (420 mg, 1.56 mmol) in dioxane (10 ml). The reaction mixture was stirred for 1 hour at room temperature. Another portion of phosphorus(III) tribromide (0.41 ml, 4.37 mmol) was added. The reaction mixture was stirred for 16 hours at room temperature. It was cooled to 0° C. Water (5 ml) was added dropwise. The reaction mixture was warmed to room temperature and diluted with ethyl acetate (400 ml). It was washed with a 10% aqueous solution of sodium hydrogensulphate. The aqueous phase was extracted with ethyl acetate (50 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (100 g), using ethyl acetate/heptane 1:3 as eluent, to give 297 mg of 2-(2,4-dichlorophenoxy)benzyl bromide. The reaction mixture was stirred for 16 hours at room temperature It was cooled to 0° C The reaction mixture was warmed to room temperature It was washed with a 10% aqueous solution of sodium hydrogensulphate The aqueous phase was extracted with ethyl acetate (50 ml) The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) dried over magnesium sulphate The solvent was removed in vacuo The crude product was purified by flash chromatography on silica (100 g)

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

Procedure: Sodium borohydride (119 mg, 3.15 mmol) was added to a solution of 2-(2,4-dichlorophenoxy)benzaldehyde (600 mg, 2.25 mmol) in isopropanol (10 ml) and DCM (20 ml). The reaction mixture was stirred for 2 hours at room temperature. A 10% aqueous solution of sodium hydrogensulphate (200 ml) was added dropwise. Ethyl acetate (300 ml) was added successively. The phases were separated. The aqueous phase was extracted with ethyl acetate (100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (100 g), using ethyl acetate/heptane 1:3 as eluent, to give 440 mg of 1-[2-(2,4-dichlorophenoxy)phenyl]methanol. The phases were separated The aqueous phase was extracted with ethyl acetate (100 ml) The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) dried over magnesium sulphate The solvent was removed in vacuo The crude product was purified by flash chromatography on silica (100 g)