(3-chloro-5-iodophenyl)methanol

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 stirred ice-cooled solution of triphenylphosphine in 10 mL of CH2Cl2 was added dropwise a solution of bromine in 5 ml of CH2Cl2. After the reaction mixture was stirred at room temperature for 30 min and cooled at ice bath temperature, a solution of the above (3-chloro-5-iodo-phenyl)-methanol in 15 ml of CH2Cl2 was added dropwise. The reaction mixture was stirred 0° C. for another 1 h and concentrated. The residue was washed with hexane several times and the combined hexane layer was concentrated to give 1-bromomethyl-3-chloro-5-iodo-benzene (1.2 g, 97%). cooled at ice bath temperature The reaction mixture was stirred 0° C. for another 1 h concentrated The residue was washed with hexane several times the combined hexane layer was concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 3-chloro-5-iodobenzoate was dissolved in anhydrous THF and cooled to 0° C. 1M DIBAL in toluene (13 mL) was added slowly to the reaction solution at that temperature. The reaction mixture was stirred overnight at room temperature. Next morning, another 10 mL of 1M DIBAL in toluene was added and stirred for additional 4 h. When the reaction was complete, the reaction mixture was quenched with saturated solution of potassium sodium tartrate. The reaction mixture wad then extracted with ethyl acetate (×3). The combined organic extracts were dried over Na2SO4 and concentrated to afford the desired (3-chloro-5-iodo-phenyl)-methanol (2.7 g, 98%). stirred for additional 4 h the reaction mixture was quenched with saturated solution of potassium sodium tartrate The reaction mixture wad then extracted with ethyl acetate (×3) The combined organic extracts were dried over Na2SO4 concentrated