Water → 12-bromo-7H-dibenzo[a,g]carbazole

HRID 530763Notes

Reaction equation

HRID 530763 reaction equation
[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[CH:3][CH:2]=1)[NH:14][C:13]1[C:8]3=[CH:9][CH:10]=[C:11]2[CH:21]=[CH:20][CH:19]=[CH:18][C:12]2=1.[Br:22]Br.O>ClCCl>[Br:22][C:10]1[CH:9]=[C:8]2[C:13]([NH:14][C:15]3[C:7]2=[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=[CH:17][CH:16]=3)=[C:12]2[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=12

Participants

5

Reactant 3

HCID 962WaterHCID 91607H-Dibenzo[a,g]carbazoleHCID 24408Bromine

Product 1

HCID 7126902012-bromo-7H-dibenzo[a,g]carbazoleYield 160.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10.3 g of 7H-dibenzo[a,g]carbazole was dissolved in dichloromethane (150 mL) at 0° C. with stirring. To this was dropped a dichloromethane solution of bromine (3.1 g in dichloromethane). After being stirred at room temperature for 2 h, the solution was poured into 200 mL of water, filtered, and washed with 500 mL water. The white residue was recrystallized in ethanol and yielded 12-bromo-7H-dibenzo[a,g]carbazole as colorless crystals (10.8 g).

Workup

  1. stirringAfter being stirred at room temperature for 2 h
  2. filtrationfiltered
  3. washwashed with 500 mL water
  4. customThe white residue was recrystallized in ethanol

Sources & evidence

ORD record
ord-47903db35f584d6982b1b97ac30c13dd
Source dataset
uspto-grants-2016_05
Patent number
US09353085B2

Reaction notes

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