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

HRID 419460ノート

反応式

HRID 419460 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 536287222-Methoxy-1-nitro-4-vinylbenzene収率 58%

試薬・触媒・溶媒 1

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

反応条件

温度
100 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5d314b0e4aae41de8b67b93189d98378
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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