تفاعل #45573

معادلة التفاعل

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2,2-trifluoroacetamide

2-phenyl-1,3,2-dioxaborinane

tripotassium phosphate

→

compound

المردود 84.0%

N-(2-Bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)2,2,2-trifluoroacetamide

المردود 84.0%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىby purging with nitrogen, N,N-dimethylformamide (50 ml)
2. 2
   أخرىwas injected into it with a syringe
3. 3
   درجة الحرارةAfter cooling
4. 4
   أخرىthe reaction liquid
5. 5
   غسيلsuccessively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine
6. 6
   تجفيفThe organic layer was dried on anhydrous magnesium sulfate
7. 7
   تركيزthe solvent was concentrated under reduced pressure
8. 8
   أخرىto obtain a brown residue
9. 9
   أخرىThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

الإجراء التجريبي

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2,2-trifluoroacetamide (I-36) (1.29 g, 2.79 mmol), 2-phenyl-1,3,2-dioxaborinane (474 mg, 2.93 mmol), tripotassium phosphate (74-85%, 1.48 g, 5.58 mmol) and tetrakis(triphenylphosphine)palladium(0) (406 mg, 0.352 mmol) were added to a 30-ml eggplant-type flask, followed by purging with nitrogen, N,N-dimethylformamide (50 ml) was injected into it with a syringe, followed by stirring overnight at 95° C. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine, an aqueous saturated sodium hydrogencarbonate solution and saturated brine. The organic layer was dried on anhydrous magnesium sulfate, then the solvent was concentrated under reduced pressure to obtain a brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) to obtain the entitled compound (968 mg, 84%) as a brown solid.

المصدر