Styrene → trans-Stilbene

HRID 429612노트

반응식

HRID 429612 반응식
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

참가 물질

9

반응물 3

HCID 7501StyreneHCID 214133-BromoquinolineHCID 517045Sodium Acetate

생성물 4

HCID 107401,1-Diphenylethylene수율 14.1%HCID 214133-BromoquinolineHCID 638088trans-Stilbene수율 85.1%HCID 5356785cis-Stilbene수율 0.8%

시약·촉매·용매 2

HCID 164911Tetraphenylphosphonium Chloride촉매HCID 6228Dimethylformamide용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-dd08380619e74406b89f84d676a720ba
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316675B1

반응 노트

불러오는 중…