Water → 7-Bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275924Notes

Reaction equation

HRID 2275924 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2=[CH:11][C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=[C:9]2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4.C1C(=O)N([Br:30])C(=O)C1.O>C(#N)C>[Br:30][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH:11]=[C:10]3[C:2]([CH3:22])([CH3:1])[C:3]4[C:8]([C:9]3=[CH:21][C:20]2=1)=[CH:7][CH:6]=[CH:5][CH:4]=4

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 665852047,7-Dimethyl-5,7-dihydroindeno[2,1-b]carbazole

Product 1

HCID 667977897-Bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

66.5 g (234.6 mmol) of 12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]-fluorene are initially introduced in 1000 ml of acetonitrile. A solution of 41.7 g (234.6 mmol) of NBS in 500 ml of CH3CN is subsequently added dropwise at −15° C. with exclusion of light, allowed to come to RT and stirred at this temperature for a further 4 h. 150 ml of water are subsequently added to the mixture, which is then extracted with CH2Cl2. The organic phase is dried over MgSO4, and the solvents are removed in vacuo. The product is washed by stirring with hot hexane and filtered off with suction. Yield: 47.5 g (131 mmol), 55.9% of theory, purity according to 1H-NMR approx. 97%.

Workup

  1. customto come to RT
  2. extractionis then extracted with CH2Cl2
  3. dry with materialThe organic phase is dried over MgSO4
  4. customthe solvents are removed in vacuo
  5. washThe product is washed
  6. stirringby stirring with hot hexane
  7. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-ddbf9e210e184495b6064064c791f0ed
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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