Styrene → 3-Nitrostilbene

HRID 578772ノート

反応式

HRID 578772 の反応式
Br[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(NC(C)C)(C)C>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]1(/[CH:12]=[CH:11]/[C:2]2[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 7501StyreneHCID 7912DiisopropylamineHCID 11457Benzene, 1-bromo-3-nitro-HCID 80271Tri-o-tolylphosphine

生成物 1

HCID 9775603-Nitrostilbene

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 3-bromonitrobenzene (1 g), styrene (1.7 mL), palladium(II) acetate (95 mg), tris(2-methylphenyl)phosphine (0.3 g) and N,N-diisopropylamine (5 mL) was heated for reflux for 24 hours. The reaction mixture was diluted with diethyl ether, and the resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate =10/1) to give 3-((E)-2-phenylvinyl)nitrobenzene (0.76 g). To the solution of the obtained 3-((E)-2-phenylvinyl)nitrobenzene (0.26 g) in methanol (10 mL) was added 10% palladium-carbon powder (50 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (0.22 g).

後処理

  1. temperaturewas heated
  2. temperaturefor reflux for 24 hours
  3. washthe resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate =10/1)

出典と根拠

ORDレコード
ord-e8c8c7ead0e2453c861377c3d3896e71
出典データセット
uspto-grants-2015_05
特許番号
US09040693B2

反応ノート

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