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ChemicalBook CAS DataBase List ACIFLUORFEN METHYL ESTER

ACIFLUORFEN METHYL ESTER synthesis

6synthesis methods
-

Yield:50594-67-7 84%

Reaction Conditions:

with potassium carbonate;dimethyl sulfoxide

Steps:

1.B Methyl 5(2-chloro-4-trifluoromethylphenoxy)2-nitrobenzoate

EXAMPLE 1B Methyl 5(2-chloro-4-trifluoromethylphenoxy)2-nitrobenzoate To a 5-liter, 4-necked flask fitted with a stirrer, thermometer, addition funnel, reflux condenser and drying tube is added dimethyl sulfoxide (200 ml), 2-chloro-4-trifluoromethylphenol) (715 g, 3.64 mole), and anhydrous potassium carbonate (520 g, 3.72 moles). The reaction mixture is stirred at room temperature overnight under a nitrogen atmosphere. Then methyl 5-fluoro-2-nitrobenzoate (724 g, 3.64 moles) is added over a 1 hour period (slight exotherm to 31° C.). After stirring overnight at room temperature, the inorganic solids are removed by filtration and 1700 ml of dimethyl sulfoxide removed under vacuum (1 mm, pot temp. of 85° C., vapor temp. of -40° C.). The residue is diluted with a large volume of carbon tetrachloride and water washed. The organic layer is dried with anhydrous magnesium sulfate and the solvent removed under vacuum to afford 1142 g of methyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (84% yield). Anal. Calcd. for C15 H9 ClF3 NO5: C, 47.90; H, 2.42; Cl, 9.45; F, 15.20; N, 3.73. Found: C, 47.83; H, 2.47; Cl, 9.15; L F, 14.84; N, 3.69.

References:

US4259510,1981,A

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