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ChemicalBook CAS DataBase List 4-BROMOPHENYL TRIFLUOROMETHANESULFONATE
129112-25-0

4-BROMOPHENYL TRIFLUOROMETHANESULFONATE synthesis

3synthesis methods
-

Yield: 96.5%

Reaction Conditions:

with pyridine;hydrogenchloride;trifluoromethanesulfonic acid anhydride in dichloromethane

Steps:

1.a (a)
(a) Synthesis of 2-(trifluoromethanesulfonyl)oxy-bromobenzene (5) Into a four-neck flask was weighed 250.00 g (1.445 mol) of 2-bromophenol, and the atmosphere of the reaction vessel fitted with a thermometer, a condenser tube, and a dropping funnel with a pressure-equalizing tube was completely replaced with nitrogen. Thereto were added 1,500 mL of anhydrous methylene chloride and 171.40 g (2.168 mol) of pyridine, followed by cooling to 0° C. After the dropwise addition of 448.45 g (1.590 mol) of trifluoromethanesulfonic anhydride over a period of 2 hours, the whole was stirred at room temperature for 2 hours. The resulting mixed solution was poured into 500 mL of 2N hydrochloric acid aqueous solution, the mixture was stirred at room temperature for 30 minutes, and then the layers were separated from each other. The resulting organic layer was washed with water and saturated saline and dried over anhydrous magnesium, and then the solvent was removed by evaporation under reduced pressure. The residue was purified by distillation under reduced pressure to obtain the title compound (425.32 g, a colorless oily substance). Yield 96.5%. bp: 112-113° C./1995-2128Pa 1H NMR (CDC3): δ; 7.2-7.4 (m, 3H), 7.6-7.8 (m, 1H)

References:

Matsumura, Kazuhiko;Saito, Takao US2003/144138, 2003, A1

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