ChemicalBook CAS DataBase List 3-Fluoro-4-methylbenzoic acid

3-Fluoro-4-methylbenzoic acid synthesis

9synthesis methods

Product Name:3-Fluoro-4-methylbenzoic acid
CAS Number:350-28-7
Molecular formula:C8H7FO2
Molecular Weight:154.14

In a Schlenk (50 mL) reaction flask with a carbon dioxide balloon attached at the stub, Cu(OAc)2.H2O (0.0125 mmol), 1,2-bis(diphenylphosphino)benzene (0.018 mmol), and 1,4-dioxane (2.0 mL) were added with stirring, and then the flask was placed at 60 °C o

51436-99-8 Synthesis

51436-99-8
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124-38-9
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350-28-7
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$8.00/1g

Yield:350-28-7 84%

Reaction Conditions:

Stage #1:carbon dioxide with o-phenylenebis(diphenylphosphine);copper(II) acetate monohydrate in 1,4-dioxane at 60; for 0.416667 h;Schlenk technique;
Stage #2:2-fluoro-4-bromotoluene with palladium diacetate;triethylamine;4,5-bis(diphenylphosphino)-9,9-dimethylxanthene in 1,4-dioxane;toluene at 100; for 4 h;Schlenk technique;

Steps:

9 Preparation of benzoic acid
General procedure: In a Schlenk (50 mL) reaction flask with a carbon dioxide balloon attached to a branch tube, add Cu (OAc) 2.H2O (0.0125 mmol), 1,2-bis (diphenylphosphine) benzene (0.018 mmol), and 1,4 -Dioxane (2.0mL), PMHS (2.5mmol) was added under stirring, and then the reaction flask was placed in an oil bath at 60 ° C for 25min to react under carbon dioxide atmosphere, followed by toluene (8mL) and bromobenzene (1.0 mmol), Pd (OAc) 2 (0.03 mmol), 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (0.06 mmol), Et3N (2.5 mmol, 2.5 equiva.), The carbon dioxide was then removed and reacted at 100 ° C until the raw bromobenzene disappeared. After cooling to room temperature, sodium hydroxide solution (1M, 10.0mL) was added, stirred for 10min, and filtered. The solid was washed three times with water, and the filtrate was washed with ethyl acetate ( 2 × 10mL) left after extraction, the aqueous layer was adjusted to pH 1-2 with hydrochloric acid solution (1M), extracted with ethyl acetate (3 × 15mL), dried over anhydrous sodium sulfate,The solvent was removed to give benzoic acid. Yield, 65%.

References:

Dalian Institute of Chemical Physics;Li Can;Lu Shengmei;Ku Malasiwami·palidala;Wang Mengmeng CN110724047, 2020, A Location in patent:Paragraph 0085-0086; 0109-0111; 0176

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201230-82-2 Synthesis