반응 #45573

반응 방정식

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

2-phenyl-1,3,2-dioxaborinane

tripotassium phosphate

→

compound

수율 84.0%

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

수율 84.0%

용매

ethyl acetate

반응 조건

후처리

1. 1
   기타by purging with nitrogen, N,N-dimethylformamide (50 ml)
2. 2
   기타was injected into it with a syringe
3. 3
   온도After cooling
4. 4
   기타the reaction liquid
5. 5
   세척successively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine
6. 6
   건조The organic layer was dried on anhydrous magnesium sulfate
7. 7
   농축the solvent was concentrated under reduced pressure
8. 8
   기타to obtain a brown residue
9. 9
   기타The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

실험 절차

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.

출처