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

HRID 1483190노트

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HRID 1483190 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][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:5]1[CH:6]=[CH:7][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:3][CH:4]=1)([O-:10])=[O:9]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 124951-Iodo-4-nitrobenzeneHCID 725452334-Bromo-3,5-dimethylphenyl propiolate

생성물 1

HCID 725454764-Bromo-3,5-dimethylphenyl 3-(4-nitrophenyl)propiolate수율 74%

시약·촉매·용매 2

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

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온도
65 °C

실험 절차

1-Iodo-4-nitrobenzene (550 mg, 2.17 mmol) in THF (4 mL) was degassed under reduced pressure at −78° C., and then nitrogen gas was introduced. To the solution was added K2CO3 (552 mg, 298.6 mmol), CuI (30 mg, 0.16 mmol) and PdCl2(Ph3P)2 (14 mg, 0.020 mmol), and the mixture was stirred at 65° C. 4-bromo-3,5-dimethylphenyl propiolate (6-1) (506 mg, 2.03 mmol) in THF (2.5 mL) was added by syringe pump over a period of 6 h. After being cooled to room temperature, the mixture was filtered and washed with EtOAc. The filtrate was concentrated and purified by silica gel column chromatography to give the title compound 7-1 (551 mg, 74% yield) as a brown solid.

후처리

  1. additionnitrogen gas was introduced
  2. temperatureAfter being cooled to room temperature
  3. filtrationthe mixture was filtered
  4. washwashed with EtOAc
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-cb9e5fa46bd34dd29ce6afa7a9084312
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416121B2

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