Tris(1,1-dimethylethyl)phosphine → HCID 66797731, compound

HRID 2275961Notes

Reaction equation

HRID 2275961 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C:26]4[CH:25]=[C:24]5[C:27]([CH3:35])([CH3:34])[C:28]6[C:33]([C:23]5=[CH:22][C:21]=4[C:20]4[C:15]3=[CH:16][CH:17]=[CH:18][CH:19]=4)=[CH:32][CH:31]=[CH:30][CH:29]=6)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:36]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:41]=[CH:40][C:39]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[CH:45][CH:44]=2)=[CH:38][CH:37]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:46]1([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:45]=[CH:44][C:43]([N:42]([C:39]2[CH:40]=[CH:41][C:36]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[CH:37][CH:38]=2)[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([N:14]4[C:26]5[CH:25]=[C:24]6[C:27]([CH3:35])([CH3:34])[C:28]7[C:33]([C:23]6=[CH:22][C:21]=5[C:20]5[C:15]4=[CH:16][CH:17]=[CH:18][CH:19]=5)=[CH:32][CH:31]=[CH:30][CH:29]=7)=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:48][CH:47]=1

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 504244Bis-biphenyl-4-yl-amineHCID 23676156Sodium t-butoxideHCID 66797677HCID 66797677, compound

Product 1

HCID 66797731HCID 66797731, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

10 g (19.4 mmol) of 10-(4′-bromobiphenyl-4-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene are dissolved in 300 ml of toluene with 9.6 g (30 mmol) of bis(4-biphenylyl)amine and degassed. 1.94 ml (1.94 mmol/1 M in toluene) of tri-tert-butylphosphine, 252 mg of Pd(OAc)2 and 4.1 g (41.7 mmol) of NaOt-Bu are added, and the mixture is stirred under reflux for 10 h. The mixture is filtered through Alox B (activity grade 1), washed with water, dried and evaporated. The crude product is extracted with toluene in a Soxhlet extractor, recrystallised from toluene/heptane, giving 6.7 g (8.9 mmol, 46%) of the product as a yellow solid. Finally, the product is sublimed in a high vacuum, the purity is 99.9%.

Workup

  1. customdegassed
  2. temperatureunder reflux for 10 h
  3. filtrationThe mixture is filtered through Alox B (activity grade 1)
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. extractionThe crude product is extracted with toluene in a Soxhlet extractor
  8. customrecrystallised from toluene/heptane

Sources & evidence

ORD record
ord-86377fd709e945f68e43ec13ba0a7d6a
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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