Sodium Carbonate → 2-Bromo-7,7-dimethyl-5-phenyl-5,7-dihydroindeno[2,1-b]carbazole

HRID 2275911Notes

Reaction equation

HRID 2275911 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1([CH3:36])[C:18]2=[CH:19][C:20]3[N:21]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:22]4[C:27]([C:28]=3[CH:29]=[C:17]2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:26][CH:25]=[CH:24][CH:23]=4.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:1][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:20]1[CH:19]=[C:18]3[C:10]([CH3:36])([CH3:9])[C:11]4[C:16]([C:17]3=[CH:29][C:28]2=1)=[CH:15][CH:14]=[CH:13][CH:12]=4

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 6679800712,12-Dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Product 1

HCID 667976632-Bromo-7,7-dimethyl-5-phenyl-5,7-dihydroindeno[2,1-b]carbazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9.51 g (54 mmol) of N-bromosuccinimide are added over the course of 15 min to a solution of 19.3 g (54 mmol) of 12,12-dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene in 80 ml of chloroform at RT under a protective-gas atmosphere and with exclusion of light. The mixture is stirred for 6 h, 80 ml of sat. Na2CO3 soln. are subsequently added, and the organic phase is separated off and dried over Na2SO4. After removal of the solvent under reduced pressure, the residue is recrystallised, giving the product as a colourless solid in a yield of 20 g (45 mmol), 85%.

Workup

  1. additionare subsequently added
  2. customthe organic phase is separated off
  3. dry with materialdried over Na2SO4
  4. customAfter removal of the solvent under reduced pressure
  5. customthe residue is recrystallised

Sources & evidence

ORD record
ord-c10f8ec23731447d9dc4fd12a4ae52d8
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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