Bromobenzene → HCID 66797829, compound

HRID 2275946Notes

Reaction equation

HRID 2275946 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]([N:19]3[C:31]4[CH:30]=[C:29]5[C:32]([CH3:62])([CH3:61])[C:33]6[C:38]([C:28]5=[CH:27][C:26]=4[C:25]4[C:20]3=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:37][CH:36]=[CH:35][C:34]=6[C:39]3[CH:40]=[C:41]4[C:49](=[CH:50][CH:51]=3)[NH:48][C:47]3[CH:46]=[C:45]5[C:52]([CH3:60])([CH3:59])[C:53]6[C:58]([C:44]5=[CH:43][C:42]4=3)=[CH:57][CH:56]=[CH:55][CH:54]=6)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.CC([O-])(C)C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>CC1C=CC(C)=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:13]1([C:11]2[N:12]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=[C:9]([N:19]3[C:31]4[CH:30]=[C:29]5[C:32]([CH3:62])([CH3:61])[C:33]6[C:38]([C:28]5=[CH:27][C:26]=4[C:25]4[C:20]3=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:37][CH:36]=[CH:35][C:34]=6[C:39]3[CH:40]=[C:41]4[C:49](=[CH:50][CH:51]=3)[N:48]([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[C:47]3[CH:46]=[C:45]5[C:52]([CH3:60])([CH3:59])[C:53]6[C:58]([C:44]5=[CH:43][C:42]4=3)=[CH:57][CH:56]=[CH:55][CH:54]=6)[N:10]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 66797653HCID 66797653, compound

Product 1

HCID 66797829HCID 66797829, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

21.0 g (26 mmol) of 7-{10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorenyl}-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene, 2.8 g (27 mmol) of bromobenzene and 6.8 g (71 mmol) of NaOtBu are suspended in 1000 ml of p-xylene. 0.11 g (0.5 mmol) of Pd(OAc)2 and 0.33 ml of a 1 M tri-tert-butylphosphine solution are added to this suspension. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, washed three times with 100 ml of water and subsequently evaporated to dryness. The residue is extracted with hot toluene, recrystallised from toluene and finally sublimed in a high vacuum. The yield is 15.3 g (18 mmol, 66.5%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed three times with 100 ml of water
  6. customsubsequently evaporated to dryness
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised from toluene

Sources & evidence

ORD record
ord-5a70fffef43d405682eb080f2b2cef42
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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