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

HRID 877291

Reaction equation

HRID 877291 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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.)

Sources & evidence

ORD record
ord-52646a4582bf43ba9c9fb5c133992734
Source dataset
uspto-grants-2015_03
Patent number
US08986852B2

Linked notes

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