Water → HCID 66798025, compound

HRID 2275947Notes

Reaction equation

HRID 2275947 reaction equation
[CH3:1][C:2]1([CH3:56])[C:10]2=[CH:11][C:12]3[N:13]([C:22]4[CH:27]=[CH:26][C:25]([C:28]5[CH:33]=[CH:32][C:31]([N:34]6[C:46]7[CH:45]=[C:44]8[C:47]([CH3:55])([CH3:54])[C:48]9[C:53]([C:43]8=[CH:42][C:41]=7[C:40]7[C:35]6=[CH:36][CH:37]=[CH:38][CH:39]=7)=[CH:52][CH:51]=[CH:50][CH:49]=9)=[CH:30][CH:29]=5)=[CH:24][CH:23]=4)[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:64])C(=O)C1.O>C1COCC1>[Br:64][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:22]1[CH:27]=[CH:26][C:25]([C:28]3[CH:29]=[CH:30][C:31]([N:34]4[C:46]5[CH:45]=[C:44]6[C:47]([CH3:55])([CH3:54])[C:48]7[C:53]([C:43]6=[CH:42][C:41]=5[C:40]5[C:35]4=[CH:36][CH:37]=[CH:38][CH:39]=5)=[CH:52][CH:51]=[CH:50][CH:49]=7)=[CH:32][CH:33]=3)=[CH:24][CH:23]=1)[C:12]1[CH:11]=[C:10]3[C:2]([CH3:56])([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 66798000HCID 66798000, compound

Product 1

HCID 66798025HCID 66798025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

9.42 g (13.1 mmol) of 4,4′-bis(12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-10-yl)biphenyl are initially introduced in 77 ml of THF. A solution of 2.36 g (13.2 mmol) of NBS in 25 ml of THF is subsequently added dropwise at −15° C. with exclusion of light, allowed to come to room temperature 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 ethanol and filtered off with suction. The yield is 7.5 g (9.4 mmol, 72%).

Workup

  1. customto come to room temperature
  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 ethanol
  7. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-aaed83bab57d40038903ce843359ecad
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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