Nitrogen → Dimethyl 2-bromo-5-carbazol-9-ylterephthalate

HRID 1485597Notes

Reaction equation

Br[C:2]1[C:3]([Br:18])=[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].[CH:19]1[C:31]2[NH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1.N#N.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1Cl.[Cu].O>[Br:18][C:3]1[CH:2]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[C:11]([N:30]2[C:31]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[C:24]3[C:29]2=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:10][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 170 °C

Procedure

A degassed solution of 157.6 g (400 mmol) of diethyl dibromoterephthalate and 36.7 g (220 mmol) of carbazole in 1 l of 1,2-dichlorobenzene is saturated with N2 for 1 h. Then, firstly 20 g (314 mmol) of copper powder, then 18 g (67 mmol) of 18-crown-6 are added to the solution, and 177 g (850 mmol) of potassium carbonate as the solid are subsequently added. The reaction mixture is heated at 170° C. for 18 h. After cooling to room temperature, 1 l of water is carefully added. The organic phase is washed with 4×50 ml of H2O and dried over MgSO4, and the solvents are removed in vacuo. The pure product is obtained by recrystallisation. The yield is 83 g (177 mmol), corresponding to 81% of theory.

Workup

additionare subsequently added
temperatureAfter cooling to room temperature
washThe organic phase is washed with 4×50 ml of H2O
dry with materialdried over MgSO4
customthe solvents are removed in vacuo
customThe pure product is obtained by recrystallisation

Sources & evidence

ORD record: ord-28d12380c0fa47bdbec00aaf7fca01ab
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422287B2

Reaction notes

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