Diethyl dibromoterephthalate → Dimethyl 2,5-bis-(9'-phenyl-9'H-[3,3']bicarbazolyl-9-yl)terephthalate

HRID 1485595Notes

Reaction equation

Br[C:2]1[C:3](Br)=[C:4]([CH:10]=[CH:11][C:12]=1[C:13]([O:15][CH2:16]C)=[O:14])[C:5]([O:7][CH2:8]C)=[O:6].[C:19]1([N:25]2[C:37]3[CH:36]=[CH:35][C:34](=[C:38]4[CH:50]=[C:49]5[C:41](=[N:42][C:43]6[C:48]5=[CH:47][CH:46]=[CH:45][CH:44]=6)[CH:40]=[CH:39]4)[CH2:33][C:32]=3[C:31]3[C:26]2=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:19]1([N:25]2[C:37]3[CH:36]=[CH:35][C:34]([C:38]4[CH:39]=[CH:40][C:41]5[N:42]([C:3]6[CH:2]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[C:11]([N:42]7[C:41]8[CH:40]=[CH:39][C:38]([C:34]9[CH:35]=[CH:36][C:37]%10[N:25]([C:19]%11[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=%11)[C:26]%11[C:31]([C:32]=%10[CH:33]=9)=[CH:30][CH:29]=[CH:28][CH:27]=%11)=[CH:50][C:49]=8[C:48]8[C:43]7=[CH:44][CH:45]=[CH:46][CH:47]=8)=[CH:10][C:4]=6[C:5]([O:7][CH3:8])=[O:6])[C:43]6[C:48]([C:49]=5[CH:50]=4)=[CH:47][CH:46]=[CH:45][CH:44]=6)=[CH:33][C:32]=3[C:31]3[C:26]2=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 2

HCID 66645638Diethyl dibromoterephthalate

HCID 866760523-(9-phenyl-4H-carbazol-3-ylidene)carbazole

Product 1

HCID 86676051Dimethyl 2,5-bis-(9'-phenyl-9'H-[3,3']bicarbazolyl-9-yl)terephthalate

Procedure

The compound is synthesised by the same procedure as for the corresponding step of Example 5 by reaction of 13.6 g (43 mmol) of diethyl dibromoterephthalate and 39 g (95.9 mmol) of 9-phenyl-3,3′-bicarbazole. The pure product is obtained by recrystallisation. The yield is 31 g (31 mmol), corresponding to 80% of theory.

Workup

customThe pure product is obtained by recrystallisation

Sources & evidence

ORD record: ord-6904faf99752439e8f323798e4e07c1a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422287B2

Reaction notes

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