Carbazole → 9-[(4-Ethenylphenyl)methyl]-9H-carbazole

HRID 413943노트

반응식

HRID 413943 반응식
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1)=[CH2:15].[OH-].[Na+]>C1C=CC=CC=1.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH:10]1[C:11]2[N:12]([CH2:20][C:19]3[CH:22]=[CH:23][C:16]([CH:14]=[CH2:15])=[CH:17][CH:18]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 3

HCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 74126p-Vinylbenzyl chloride

생성물 1

HCID 187617079-[(4-Ethenylphenyl)methyl]-9H-carbazole수율 80%

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 22272175Benzene--water (1/1)용매

실험 절차

Carbazole was reacted with 1.5-fold excess of 4-vinylbenzyl chloride in benzene/water using NaOH as a base, and benzyltriethylammonium chloride as phase catalyst to afford 4-(9-carbazolyl)methylstyrene (CMS) at 80° C. for 5 h. The reaction mixture was extracted with chloroform and the organic layer washed with water, evaporated, and washed with hexane several times. The solid was dissolved in and recrystallized from diethyl ether at −20° C. Yield: 80%. The solid monomer was dried over P205 at 10-6 mmHg for 1 week and then dissolved in anhydrous THF and stored at −30° C. in glass ampoules under high vacuum. This reaction scheme is schematically shown in FIG. 2. The monomer is characterized by using 1H-NMR, 13C-NMR and FT-IR. Undesirable side-reaction of the monomer prepared is seen in FIG. 1.

출처 및 근거

ORD 기록
ord-bff8bda8e32043c4b05ee86bb71eb60e
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06569978B2

반응 노트

불러오는 중…