Sodium Carbonate → HCID 66715492, compound

HRID 1530742Notes

Reaction equation

HRID 1530742 reaction equation
[CH3:1][C:2]1([CH3:41])[C:14]2[CH:13]=[C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:23]=[CH:24][C:25]5[N:26]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:27]6[C:32]([C:33]=5[CH:34]=4)=[CH:31][CH:30]=[CH:29][CH:28]=6)=[CH:18][CH:17]=3)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[Br:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52](I)=[CH:51][CH:50]=2)=[CH:45][CH:44]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:42][C:43]1[CH:44]=[CH:45][C:46]([C:49]2[CH:54]=[CH:53][C:52]([N:15]([C:12]3[CH:11]=[CH:10][C:9]4[C:8]5[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=5)[C:2]([CH3:41])([CH3:1])[C:14]=4[CH:13]=3)[C:16]3[CH:17]=[CH:18][C:19]([C:22]4[CH:23]=[CH:24][C:25]5[N:26]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:27]6[C:32]([C:33]=5[CH:34]=4)=[CH:31][CH:30]=[CH:29][CH:28]=6)=[CH:20][CH:21]=3)=[CH:51][CH:50]=2)=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 109044524-Bromo-4'-iodobiphenylHCID 580508019,9-Dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Product 1

HCID 66715492HCID 66715492, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30 g (57 mmol) (9,9-dimethyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)-phenyl]-amine and 20 g (57 mmol) 4-bromo-4′-iodo-biphenyl [105946-82-5] are dissolved in 200 ml toluene and treated with 100 ml of a 2 M solution of sodium carbonate. The reaction mixture is carefully degassed and 200 mg tetrakistriphenylphosphine palladiume are added and refluxed for 20 h. The reaction mixture is then cooled to room temperature and 250 ml water is added. The layers are separated. The water phase is then extracted three times with toluene. The organic layers are then washed twice with water, dried over magnesium sulphate, filtrated and the solvent is then removed under vacuum. The residue is recrystallized from butanole/toluene, to yield 29 g (38 mmol) (67%) of a white solid with a purity of 99.3%.

Workup

  1. customThe reaction mixture is carefully degassed
  2. addition200 mg tetrakistriphenylphosphine palladiume are added
  3. temperaturerefluxed for 20 h
  4. addition250 ml water is added
  5. customThe layers are separated
  6. extractionThe water phase is then extracted three times with toluene
  7. washThe organic layers are then washed twice with water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltrated
  10. customthe solvent is then removed under vacuum
  11. customThe residue is recrystallized from butanole/toluene

Sources & evidence

ORD record
ord-c9f2fe0e36604d5d837cc21982d746cf
Source dataset
uspto-grants-2015_07
Patent number
US09093656B2

Reaction notes

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