2-(2,4-dichlorophenoxy)benzaldehyde

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: 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: At 0° C., a 1.2 M solution of diisobutylaluminum hydride in toluene (12.3 ml, 14.8 mmol) was added dropwise to a solution of 2-(2,4-dichlorophenoxy)benzonitrile (3.0 g, 11.3 mmol) in THF (30 ml). The reaction mixture was warmed to room temperature and stirred for 16 hours. It was cooled to 0° C. Water (10 ml) was added dropwise. It was warmed to room temperature. The solid was removed by filtration through a plug of celite. The solvent was removed from the filtrate in vacuo. The crude product was purified by flash chromatography on silica (130 g), using ethyl acetate/heptane 1:3 as eluent, to give 800 mg of 2-(2,4-dichlorophenoxy)benzaldehyde. It was cooled to 0° C It was warmed to room temperature The solid was removed by filtration through a plug of celite The solvent was removed from the filtrate in vacuo The crude product was purified by flash chromatography on silica (130 g)

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: 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: At 0° C., a 1.2 M solution of diisobutylaluminum hydride in toluene (12.3 ml, 14.8 mmol) was added dropwise to a solution of 2-(2,4-dichlorophenoxy)benzonitrile (3.0 g, 11.3 mmol) in THF (30 ml). The reaction mixture was warmed to room temperature and stirred for 16 hours. It was cooled to 0° C. Water (10 ml) was added dropwise. It was warmed to room temperature. The solid was removed by filtration through a plug of celite. The solvent was removed from the filtrate in vacuo. The crude product was purified by flash chromatography on silica (130 g), using ethyl acetate/heptane 1:3 as eluent, to give 800 mg of 2-(2,4-dichlorophenoxy)benzaldehyde. It was cooled to 0° C It was warmed to room temperature The solid was removed by filtration through a plug of celite The solvent was removed from the filtrate in vacuo The crude product was purified by flash chromatography on silica (130 g)

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

Procedure: At 0° C., a 1.2 M solution of diisobutylaluminum hydride in toluene (12.3 ml, 14.8 mmol) was added dropwise to a solution of 2-(2,4-dichlorophenoxy)benzonitrile (3.0 g, 11.3 mmol) in THF (30 ml). The reaction mixture was warmed to room temperature and stirred for 16 hours. It was cooled to 0° C. Water (10 ml) was added dropwise. It was warmed to room temperature. The solid was removed by filtration through a plug of celite. The solvent was removed from the filtrate in vacuo. The crude product was purified by flash chromatography on silica (130 g), using ethyl acetate/heptane 1:3 as eluent, to give 800 mg of 2-(2,4-dichlorophenoxy)benzaldehyde. It was cooled to 0° C It was warmed to room temperature The solid was removed by filtration through a plug of celite The solvent was removed from the filtrate in vacuo The crude product was purified by flash chromatography on silica (130 g)

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

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: At 0° C., a 1.2 M solution of diisobutylaluminum hydride in toluene (12.3 ml, 14.8 mmol) was added dropwise to a solution of 2-(2,4-dichlorophenoxy)benzonitrile (3.0 g, 11.3 mmol) in THF (30 ml). The reaction mixture was warmed to room temperature and stirred for 16 hours. It was cooled to 0° C. Water (10 ml) was added dropwise. It was warmed to room temperature. The solid was removed by filtration through a plug of celite. The solvent was removed from the filtrate in vacuo. The crude product was purified by flash chromatography on silica (130 g), using ethyl acetate/heptane 1:3 as eluent, to give 800 mg of 2-(2,4-dichlorophenoxy)benzaldehyde. It was cooled to 0° C It was warmed to room temperature The solid was removed by filtration through a plug of celite The solvent was removed from the filtrate in vacuo The crude product was purified by flash chromatography on silica (130 g)