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ChemicalBook CAS DataBase List Benzoic acid, 3-cyano-5-(trifluoromethoxy)-
453565-91-8

Benzoic acid, 3-cyano-5-(trifluoromethoxy)- synthesis

2synthesis methods
453565-90-7 Synthesis
3-Bromo-5-(trifluoromethoxy)Benzoicacid

453565-90-7
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$25.00/1g

Benzoic acid, 3-cyano-5-(trifluoromethoxy)-

453565-91-8
25 suppliers
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Yield:-

Reaction Conditions:

with sodium hydroxide;tetrakis(triphenylphosphine)palladium (0) in methanol;ethyl acetate;N,N-dimethyl-formamide;

Steps:

2 3-Cyano-5-trifluoromethoxybenzoic Acid

3-Cyano-5-trifluoromethoxybenzoic Acid To an ether solution of 3-bromo-5-trifluoromethoxybenzoic acid (1.08 g, 3.79 mmloes), tirmethylsilylmethyl azide was added in and stirred at room temperature for 10 minutes. The reaction was quenched with methanol and passed column with 2% ethyl acetate in hexanes to give colorless oil (0.84 g). This colorless oil was mixed with zinc cyanide (0.33 g, 2.8 mmoles) and tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, 467 mg, 0.404 mmol) in N,N-dimethylformamide(10 mL) under argon at 85° C. overnight. The reaction mixture was diluted with dichloromethane and washed with water twice. The dichloromethane layer was dried and concentrated. The residue was mixed with1M sodium hydroxide (8 mL) and methanol (4 mL) and stirred at room temperature for 2 hours. The mixture was acidified with 1M HCl to pH=1~2 and extracted with ethyl acetate. The ethyl acetate layer was washed with Brine and concentrated. The residue was passed column with 2% ethyl acetate in hexanes to give 3-cyano-5-trifluoromethoxybenzoic acid, which contained 3-[imino(methoxy)methyl]-5-trifluoromethoxybenzoic acid (3:1, 145 mg, 16.6%)

References:

US2003/55085,2003,A1

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