Styrene → trans-Stilbene

HRID 429612

反応式

HRID 429612 の反応式
C([O-])(=O)C.[Na+].[Br:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[CH2:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].CN(C=O)C>[C:8]1(/[CH:7]=[CH:16]/[C:15]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:19]1(/[CH:18]=[CH:17]\[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:19]1([C:18]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH2:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Br:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

参加物

9

反応物 3

HCID 7501StyreneHCID 214133-BromoquinolineHCID 517045Sodium Acetate

生成物 4

HCID 107401,1-Diphenylethylene収率 14.1%HCID 214133-BromoquinolineHCID 638088trans-Stilbene収率 85.1%HCID 5356785cis-Stilbene収率 0.8%

試薬・触媒・溶媒 2

HCID 164911Tetraphenylphosphonium Chloride触媒HCID 6228Dimethylformamide溶媒

実験手順

A reaction is performed as described in Example 1, except that 3.9 mg (0.015 mmol) of (CH2CN)2PdCl2, 34.9 mg (0.09 mmol) of Ph4PCl, 496.0 mg (6.05 mmol) of anhydrous sodium acetate, 638.74 mg (3.07 mmol) of 3-bromoquinoline and 427.0 mg (4.1 mmol) of styrene are reacted in 1.5 ml of DMF. Stirring is performed at 130° C. for 5 hours. According to the processing described in Example 1, a 72.5% yield of Heck products (85.1% trans-stilbene, 0.8% cis-stilbene, and 14.1% 1,1-diphenylethene) is obtained with 78.5% conversion of 3-bromoquinoline.

出典と根拠

ORDレコード
ord-dd08380619e74406b89f84d676a720ba
出典データセット
uspto-grants-2001_11
特許番号
US06316675B1

関連ノート

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