Bromobenzene → HCID 66797832, compound

HRID 2275939Notes

Reaction equation

HRID 2275939 reaction equation
[C:1]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:6]=[CH:5][C:4]([N:7]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:30]=[C:31]4[C:39](=[CH:40][CH:41]=3)[NH:38][C:37]3[CH:36]=[C:35]5[C:42]([CH3:50])([CH3:49])[C:43]6[C:48]([C:34]5=[CH:33][C:32]4=3)=[CH:47][CH:46]=[CH:45][CH:44]=6)=[CH:25][CH:24]=2)[C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]([CH3:22])([CH3:21])[C:10]=3[CH:9]=2)=[CH:3][CH:2]=1.Br[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=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:1]1([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:2]=[CH:3][C:4]([N:7]([C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]([CH3:21])([CH3:22])[C:10]=3[CH:9]=2)[C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:30]=[C:31]4[C:39](=[CH:40][CH:41]=3)[N:38]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:37]3[CH:36]=[C:35]5[C:42]([CH3:49])([CH3:50])[C:43]6[C:48]([C:34]5=[CH:33][C:32]4=3)=[CH:47][CH:46]=[CH:45][CH:44]=6)=[CH:27][CH:28]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 66797821HCID 66797821, compound

Product 1

HCID 66797832HCID 66797832, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

20.0 g (27.8 mmol) of biphenyl-4-yl-[4-(12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-7-yl)phenyl]-(9,9-dimethyl-9H-fluoren-2-yl)amine are dissolved in 500 ml of toluene with 4.39 ml (41.7 mmol) of bromobenzene and degassed. 1.94 ml (1.94 mmol/1 M in toluene) of tri-tert-butylphosphine, 249.8 mg of Pd(OAc)2 and 4.01 g (41.7 mmol) of NaOtBu are added (solids are degassed in advance), and the mixture is stirred under reflux for 5 h. The warm (45° C.) mixture is filtered through Alox B (activity grade 1), washed with water, dried and evaporated. The crude product is extracted with heptane/toluene in a Soxhlet extractor and crystallised from heptane, giving, after sublimation, 14.7 g (67%) of the product as a yellowish solid having a purity of 99.9%.

Workup

  1. customdegassed
  2. custom(solids are degassed in advance)
  3. temperatureunder reflux for 5 h
  4. filtrationis filtered through Alox B (activity grade 1)
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. extractionThe crude product is extracted with heptane/toluene in a Soxhlet extractor
  9. customcrystallised from heptane
  10. customgiving

Sources & evidence

ORD record
ord-51e3392d44f040f891beade92ca4098d
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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