2-iodo-5-propan-2-ylphenol

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

Procedure: A mixture of 3-isopropylphenol (670 mg, 4.92 mmol), KIO3 (210 mg, 0.98 mmol), and I2 (500 mg, 1.97 mmol) in acetic acid was stirred for 3 days at room temperature. The solvent was removed at reduced pressure. The residue was diluted with Et2O and washed with aq. NaHCO3, aq. Na2S2O3, and brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified with flash column chromatography to give the title compound (830 mg, 64%). The solvent was removed at reduced pressure The residue was diluted with Et2O washed with aq. NaHCO3, aq. Na2S2O3, and brine The organic layer was dried over anhydrous MgSO4 filtered concentrated under reduced pressure The residue was purified with flash column chromatography

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

Procedure: A mixture of 3-isopropylphenol (670 mg, 4.92 mmol), KIO3 (210 mg, 0.98 mmol), and I2 (500 mg, 1.97 mmol) in acetic acid was stirred for 3 days at room temperature. The solvent was removed at reduced pressure. The residue was diluted with Et2O and washed with aq. NaHCO3, aq. Na2S2O3, and brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified with flash column chromatography to give the title compound (830 mg, 64%). The solvent was removed at reduced pressure The residue was diluted with Et2O washed with aq. NaHCO3, aq. Na2S2O3, and brine The organic layer was dried over anhydrous MgSO4 filtered concentrated under reduced pressure The residue was purified with flash column chromatography

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

Procedure: To a solution of 3-isopropylphenol (25.0 g, 0.184 mol) in acetic acid (200 mL), a suspension of potassium iodate (7.88 g, 0.0368 mol) in water (75 mL) and iodine (18.7 g, 0.0736 mol) were added. This reaction mixture was stirred at room temperature for 20 hours. After addition of diethyl ether (400 mL) and water (300 mL), the organic layer was separated. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogen carbonate and brine, and then dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5) to give 2-iodo-5-isopropylphenol (27.6 g, 57%) as a colorless oil. were added the organic layer was separated The organic layer was washed with water a saturated aqueous solution of sodium hydrogen carbonate and brine, and then dried over anhydrous magnesium sulfate After filtering off the desiccant the solvent was distilled off under reduced pressure The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5)