Styrene → 4-[(E)-2-Phenylvinyl]benzo[b]thiophene

HRID 15404

反応式

HRID 15404 の反応式
Br[C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]1(/[CH:12]=[CH:11]/[C:2]2[C:10]3[CH:9]=[CH:8][S:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

8

反応物 4

HCID 7501StyreneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 120942084-Bromobenzo[b]thiophene

生成物 1

HCID 231567054-[(E)-2-Phenylvinyl]benzo[b]thiophene

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-bromobenzo[b]thiophene (0.55 g), styrene (0.89 mL), triethylamine (1.81 mL), palladium(II) acetate (59 mg) and tris(2-methylphenyl)phosphine (0.16 g) in acetonitrile (10 mL) was refluxed overnight under an argon atmosphere. The reaction mixture was diluted with diethyl ether and an insoluble material was removed by filtration. The filtrate washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane-n-hexane/ethyl acetate=5/1) to give the title compound (0.56 g).

後処理

  1. temperaturewas refluxed overnight under an argon atmosphere
  2. customan insoluble material was removed by filtration
  3. washThe filtrate 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-n-hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-c9b724ccf96a4746a1af2ce58abf5586
出典データセット
uspto-grants-2010_06
特許番号
US07732596B2

関連ノート

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