Potassium Carbonate → 4-Bromo-3,5-dimethylphenyl 3-(3-nitrophenyl)propiolate

HRID 1483186노트

반응식

HRID 1483186 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([Br:29])=[C:24]([CH3:30])[CH:23]=1)(=[O:20])[C:18]#[CH:19]>C1COCC1.[Cu]I>[N+:8]([C:4]1[CH:3]=[C:2]([C:19]#[C:18][C:17]([O:21][C:22]2[CH:23]=[C:24]([CH3:30])[C:25]([Br:29])=[C:26]([CH3:28])[CH:27]=2)=[O:20])[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 125741-Iodo-3-nitrobenzeneHCID 725452334-Bromo-3,5-dimethylphenyl propiolate

생성물 1

HCID 894777654-Bromo-3,5-dimethylphenyl 3-(3-nitrophenyl)propiolate수율 29%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
65 °C

실험 절차

1-Iodo-3-nitrobenzene (41.05 g, 164.3 mmol) in THF (100 mL) was degassed under reduced pressure at −78° C., and then nitrogen gas was introduced. To the solution was added K2CO3 (41.27 g, 298.6 mmol), CuI (2.27 g, 11.9 mmol) and PdCl2(Ph3P)2 (1.11 g, 1.57 mmol), and the mixture was stirred at 65° C. 4-bromo-3,5-dimethylphenyl propiolate (6-1) (37.79 g, 149.3 mmol) in THF (68 mL) was added by syringe pump over a period of 5.4 hr, and the mixture was stirred an additional 1 h after addition was complete. After being cooled to room temperature, the mixture was filtered. The filtrate was concentrated and purified by silica gel column chromatography. The fractions containing the desired compound were concentrated. To the concentrate added hexane and the precipitated solid was collected by filtration. The solid was washed with hexane and dried to give the title compound 6-2 (15.96 g, 29% yield) as a brown solid.

후처리

  1. additionnitrogen gas was introduced
  2. stirringthe mixture was stirred an additional 1 h
  3. additionafter addition
  4. temperatureAfter being cooled to room temperature
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. additionThe fractions containing the desired compound
  9. concentrationwere concentrated
  10. additionTo the concentrate added hexane
  11. filtrationthe precipitated solid was collected by filtration
  12. washThe solid was washed with hexane
  13. customdried

출처 및 근거

ORD 기록
ord-6dbdfa8f095c4178bdd62a44f2c4d7f3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416121B2

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