1-(4-bromo-2-chlorophenyl)ethanol

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

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

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1-(4-bromo-2-chlorophenyl)ethanone (700 mg, 2998 μmol) in THF (20 mL) was added sodium borohydride (340 mg, 8994 μmol) and methanol (5 mL). Reaction suspension stirred overnight at 30° C. Reaction then partioned between EtOAc (50 mL) and sat NH4Cl (25 mL). Aqueous further extracted with EtOAc (2×25 mL). Combined organics dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 10>40% EtOAc/hexanes. Product isolated as a colorless oil. Reaction suspension Reaction Aqueous further extracted with EtOAc (2×25 mL) Combined organics dried over MgSO4 concentrated purified on silica (40 g) eluting with 10>40% EtOAc/hexanes Product isolated as a colorless oil

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1-(4-bromo-2-chlorophenyl)ethanone (700 mg, 2998 μmol) in THF (20 mL) was added sodium borohydride (340 mg, 8994 μmol) and methanol (5 mL). Reaction suspension stirred overnight at 30° C. Reaction then partioned between EtOAc (50 mL) and sat NH4Cl (25 mL). Aqueous further extracted with EtOAc (2×25 mL). Combined organics dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 10>40% EtOAc/hexanes. Product isolated as a colorless oil. Reaction suspension Reaction Aqueous further extracted with EtOAc (2×25 mL) Combined organics dried over MgSO4 concentrated purified on silica (40 g) eluting with 10>40% EtOAc/hexanes Product isolated as a colorless oil

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1-(4-bromo-2-chlorophenyl)ethanone (700 mg, 2998 μmol) in THF (20 mL) was added sodium borohydride (340 mg, 8994 μmol) and methanol (5 mL). Reaction suspension stirred overnight at 30° C. Reaction then partioned between EtOAc (50 mL) and sat NH4Cl (25 mL). Aqueous further extracted with EtOAc (2×25 mL). Combined organics dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 10>40% EtOAc/hexanes. Product isolated as a colorless oil. Reaction suspension Reaction Aqueous further extracted with EtOAc (2×25 mL) Combined organics dried over MgSO4 concentrated purified on silica (40 g) eluting with 10>40% EtOAc/hexanes Product isolated as a colorless oil

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

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1-(4-bromo-2-chlorophenyl)ethanone (700 mg, 2998 μmol) in THF (20 mL) was added sodium borohydride (340 mg, 8994 μmol) and methanol (5 mL). Reaction suspension stirred overnight at 30° C. Reaction then partioned between EtOAc (50 mL) and sat NH4Cl (25 mL). Aqueous further extracted with EtOAc (2×25 mL). Combined organics dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 10>40% EtOAc/hexanes. Product isolated as a colorless oil. Reaction suspension Reaction Aqueous further extracted with EtOAc (2×25 mL) Combined organics dried over MgSO4 concentrated purified on silica (40 g) eluting with 10>40% EtOAc/hexanes Product isolated as a colorless oil

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

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1-(4-bromo-2-chlorophenyl)ethanone (700 mg, 2998 μmol) in THF (20 mL) was added sodium borohydride (340 mg, 8994 μmol) and methanol (5 mL). Reaction suspension stirred overnight at 30° C. Reaction then partioned between EtOAc (50 mL) and sat NH4Cl (25 mL). Aqueous further extracted with EtOAc (2×25 mL). Combined organics dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 10>40% EtOAc:hexanes. Product isolated as a colorless oil. Reaction suspension Reaction Aqueous further extracted with EtOAc (2×25 mL) Combined organics dried over MgSO4 concentrated purified on silica (40 g) eluting with 10>40% EtOAc Product isolated as a colorless oil

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1-(4-bromo-2-chlorophenyl)ethanone (700 mg, 2998 μmol) in THF (20 mL) was added sodium borohydride (340 mg, 8994 μmol) and methanol (5 mL). Reaction suspension stirred overnight at 30° C. Reaction then partioned between EtOAc (50 mL) and sat NH4Cl (25 mL). Aqueous further extracted with EtOAc (2×25 mL). Combined organics dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 10>40% EtOAc/hexanes. Product isolated as a colorless oil. Reaction suspension Reaction Aqueous further extracted with EtOAc (2×25 mL) Combined organics dried over MgSO4 concentrated purified on silica (40 g) eluting with 10>40% EtOAc/hexanes Product isolated as a colorless oil

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1-(4-bromo-2-chlorophenyl)ethanone (700 mg, 2998 μmol) in THF (20 mL) was added sodium borohydride (340 mg, 8994 μmol) and methanol (5 mL). Reaction suspension stirred overnight at 30° C. Reaction then partioned between EtOAc (50 mL) and sat NH4Cl (25 mL). Aqueous further extracted with EtOAc (2×25 mL). Combined organics dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 10>40% EtOAc/hexanes. Product isolated as a colorless oil. Reaction suspension Reaction Aqueous further extracted with EtOAc (2×25 mL) Combined organics dried over MgSO4 concentrated purified on silica (40 g) eluting with 10>40% EtOAc/hexanes Product isolated as a colorless oil

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

Procedure: A solution of 1-(4-bromo-2-chlorophenyl)ethanol (1.32 g, 5.6 mmol), phenol (525 mg, 5.6 mmol) and triphenylphosphine (2198 mg, 8.4 mmol) in tetrahydrofuran (30 mL) was stirred at room temperature for 0.5 hour. Diisopropyl azodicarboxylate (1695 mg, 8.4 mmol) was dropwise to the reaction mixture and was stirred at room temperature for 12 hours. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=5:1) to give 4-bromo-2-chloro-1-(1-phenoxyethyl)benzene as a colorless oil (882 mg 54%). The mixture was concentrated to give a residue The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=5:1)