(2-chloro-4-iodophenyl)methanol

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

Procedure: 2-Chloro-4-iodobenzoic acid (5.0 g, 18 mmol) was dissolved in tetrahydrofuran (7 mL), and a solution of a borane-tetrahydrofuran complex in tetrahydrofuran (1 M, 21 mL, 23 mmol) was added at 0° C., followed by stirring at room temperature for 3 days. Water and a saturated aqueous sodium hydrogencarbonate solution were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure to afford (2-chloro-4-iodophenyl)methanol (4.8 g, 18 mmol) as a white solid (quantitative yield). followed by extraction with ethyl acetate The organic layer was washed with a saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate subsequently the solvent was distilled off under reduced pressure