Ethanol → 4-(7-Phenylbenz[a]anthracen-4-yl)-7-phenylbenz[a]anthracene

HRID 877291

반응식

HRID 877291 반응식
BrN1[C:6](=O)[CH2:5][CH2:4][C:3]1=O.[CH:9]1[C:14]2=[C:15]3[C:24](=[CH:25][CH:26]=[C:13]2[C:12]([C:27]2[C:32]4=[CH:33][CH:34]=[C:35]5[C:44]([CH:43]=[C:42]6[C:37]([CH:38]=[CH:39][CH:40]=[CH:41]6)=[CH:36]5)=[C:31]4[CH:30]=[CH:29][CH:28]=2)=[CH:11][CH:10]=1)[CH:23]=[C:22]1[C:17]([CH:18]=[CH:19][CH:20]=[CH:21]1)=[CH:16]3.[CH2:45](O)[CH3:46].[C:48]1(B(O)O)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[C:3]1([C:36]2[C:35]3[C:44]([CH:43]=[C:42]4[C:37]=2[CH:38]=[CH:39][CH:40]=[CH:41]4)=[C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([C:12]4[C:13]5=[CH:26][CH:25]=[C:24]6[C:15]([CH:16]=[C:17]7[C:22]([CH:21]=[CH:20][CH:19]=[CH:18]7)=[C:23]6[C:48]6[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=6)=[C:14]5[CH:9]=[CH:10][CH:11]=4)[C:32]2=[CH:33][CH:34]=3)[CH:46]=[CH:45][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 66827Phenylboronic AcidHCID 67184N-bromobutanimideHCID 594125524-(Benz[a]anthracen-4-yl)benz[a]anthracene

생성물 1

HCID 594127104-(7-Phenylbenz[a]anthracen-4-yl)-7-phenylbenz[a]anthracene

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

19.6 g (110 mmol) of N-bromosuccinimide are added in one portion at 100° C. with vigorous stirring to a suspension of 22.7 g (50 mmol) of 4-(benz[a]anthracen-4-yl)benz[a]anthracene in 1000 ml of DMF. The suspension is kept at 100° C. for a further 30 min. and cooled, and 1000 ml of ethanol are then added. The precipitated solid is filtered off with suction, washed three times with 100 ml of ethanol each time and dried in vacuo. The resultant solid is reacted analogously to Example 7 with 15.9 g (130 mmol) of benzeneboronic acid, Recrystallisation five times from DMF (about 6 ml/g); sublimation (p=5×10−5 mbar, T=360° C.). Yield: 21.8 g (36 mmol), 72.0%, purity 99.9% (HPLC), Tg=181.4° C.

후처리

  1. temperaturecooled
  2. filtrationThe precipitated solid is filtered off with suction
  3. washwashed three times with 100 ml of ethanol each time
  4. customdried in vacuo
  5. customsublimation (p=5×10−5 mbar, T=360° C.)

출처 및 근거

ORD 기록
ord-52646a4582bf43ba9c9fb5c133992734
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08986852B2

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