Sodium Bicarbonate → 2,7-Dibromocarbazole

HRID 219059

Reaction equation

HRID 219059 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2N)=[C:4]([NH2:16])[CH:3]=1.C([O-])(O)=O.[Na+]>P(=O)(O)(O)O>[Br:14][C:11]1[CH:12]=[CH:13][C:8]2[C:5]3[C:4](=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)[NH:16][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 112215382,2'-Diamino-4,4'-dibromobiphenyl

Product 1

HCID 111515032,7-DibromocarbazoleYield 66.2%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
190 °C

Procedure

4,4′-dibromo-2,2′-diaminobiphenyl (3.5 g, 10.23 mmol) was dissolved in phosphoric acid and heated at 190° C. for 24 hours. The reaction mixture was cooled to room temperature and then NaHCO3 (aq) was gradually added thereto to form a solid. Then, the solid was filtered to obtain 2,7-dibromocarbazole (2.2 g, 66%), the compound represented by formula e. MS [M+] 323.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto form a solid
  3. filtrationThen, the solid was filtered

Sources & evidence

ORD record
ord-ebd10a7ee021428fa542efc353b75e72
Source dataset
uspto-grants-2012_06
Patent number
US08198801B2

Linked notes

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