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 Production Method of Fluoromethyl phenyl sulfone
  • Production Method of Fluoromethyl phenyl sulfone
  • (CAS NO.: ), which is also known as , [(fluoromethyl)sulfonyl]-, could be produced through the following synthetic routes.

    Production Method of Fluoromethyl phenyl sulfone

    A. Fluoromethyl phenyl sulfide (CAS NO.: ). To a 1-L, three-necked, round-bottomed flask, equipped with a magnetic stirring bar, air condenser and thermometer are added methyl phenyl sulfoxide (25.2 g, 0.18 mol) and chloroform (150 mL). The flask is placed in a cooling bath containing 3 L of water kept at 20°C. (DAST) (38.5 g, 31.6 mL, 0.24 mol) is added to the flask, followed by antimony trichloride (0.50 g, 0.0022 mol), and an additional 50 mL of chloroform. The light yellow reaction mixture is stirred under an argon atmosphere. After 2 to 8 hr, an exothermic reaction is observed and the solution turns dark orange. The reaction mixture is poured slowly with stirring into 600 mL of ice-cold, saturated, aqueous sodium bicarbonate containing 10 g (0.25 mol) of sodium hydroxide (CAUTION: gas evolution). After 10 min, the chloroform layer is separated and the remaining aqueous layer is extracted with additional chloroform (3 × 100 mL). The combined organic layers are washed with saturated aqueous sodium bicarbonate (250 mL), saturated aqueous sodium chloride, and dried over potassium carbonate. The chloroform is removed with a rotary evaporator at 30–40°C and the crude fluoromethyl phenyl sulfide 1 (ca. 29 g), obtained as a yellow orange oil, is used immediately in the next step.

    B. Fluoromethyl phenyl sulfone (CAS NO.: ). To a 3-L, three-necked, round-bottomed flask, equipped with an overhead stirrer, thermometer, and 1-L addition funnel with sidearm are added Oxone (221.0 g, 0.36 mol) and water (700 mL). The mixture is cooled to 5°C and a solution of the crude fluoromethyl phenyl sulfide in methanol (700 mL) is placed in the addition funnel and added in a slow stream to the stirring slurry. After addition of the sulfide, the reaction mixture is stirred at room temperature for 4 hr, and the methanol is removed on a rotary evaporator at 40°C. The remaining solution is extracted with methylene chloride (2 × 500 mL). The combined organic layers are dried over magnesium sulfate, concentrated to ca. 150 mL, filtered through a plug of silica gel (230–400 mesh, 300 mL, 10 × 6.5 cm), and washed with an additional 500 mL of methylene chloride. The colorless filtrate is concentrated and the resulting oil or solid is dried under vacuum (0.1 mm) at room temperature to provide 29 g of crude fluoromethyl phenyl sulfone as a solid white mass. The solid is recrystallized from 250 mL of hot hexane (forms two layers) by cooling the two phase solution to room temperature with vigorous stirring and adding a seed crystal. The resulting white crystals of fluoromethyl phenyl sulfone (25.0–28.5 g, 80–90%) are collected by filtration, mp 53–55°C.

    Notice: All reactions should be conducted in an efficient fume hood.


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