Water → 2-Methoxy-1-nitro-4-vinylbenzene

HRID 419460노트

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HRID 419460 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].O.[CH2:14](O)[CH2:15]C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:14]=[CH2:15])[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]

참가 물질

5

반응물 3

HCID 962WaterHCID 10311-PropanolHCID 117464905-Bromo-2-nitroanisole

생성물 1

HCID 536287222-Methoxy-1-nitro-4-vinylbenzene수율 58%

시약·촉매·용매 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

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온도
100 °C

실험 절차

To 5-bromo-2-nitrophenyl methyl ether (8.0 g, 34.47 mmol) in 80 mL of n-propanol was added, PdCl2(dppf)*DCM (0.5 g, 0.69 mmol), potassium ethenyl(trifluoro)borate (6.47 g, 48.3 mmol), and TEA (3.48 g, 34.47 mmol). The mixture was heated to 100° C. for 3 h. The mixture was poured into 250 mL of H2O and extracted with DCM, dried (Na2SO4), filtered, and rotovaped down, and purified by flash chromatography to give the title compound of step B (3.58 g, 19.98 mmol, 58%). 1H NMR (400 MHz, CDCl3) δ ppm 7.82-7.87 (m, 1H), 7.02-7.07 (m, 2H), 6.70 (dd, J=17.58, 10.80 Hz, 1H), 5.87 (d, J=17.58 Hz, 1H), 5.46 (d, J=10.99 Hz, 1H), 3.97 (s, 3H).

후처리

  1. extractionextracted with DCM
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-5d314b0e4aae41de8b67b93189d98378
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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