Toluene → HCID 66797791, compound

HRID 2275958Notes

Reaction equation

HRID 2275958 reaction equation
[CH3:1][C:2]1([CH3:38])[C:10]2=[CH:11][C:12]3[N:13]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[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][C:17](B1OC(C)(C)C(C)(C)O1)=[CH:16][CH:15]=4.Br[C:40]1[CH:41]=[C:42]([C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([C:52]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[O:53])[CH:47]=2)[CH:43]=[CH:44][CH:45]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:52]([C:48]1[CH:47]=[C:46]([C:42]2[CH:43]=[CH:44][CH:45]=[C:40]([C:17]3[CH:18]=[C:19]4[C:14](=[CH:15][CH:16]=3)[N:13]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[C:12]3[CH:11]=[C:10]5[C:2]([CH3:1])([CH3:38])[C:3]6[C:8]([C:9]5=[CH:21][C:20]4=3)=[CH:7][CH:6]=[CH:5][CH:4]=6)[CH:41]=2)[CH:51]=[CH:50][CH:49]=1)(=[O:53])[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66797721HCID 66797721, compoundHCID 66798035HCID 66798035, compound

Product 1

HCID 66797791HCID 66797791, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

16.8 g (33.0 mmol) of tert-butyl 12,12-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-12H-10-azaindeno[2,1-b]fluorene-10-carboxylate, 13.4 g (40 mmol) of (3′-bromobiphenyl-3-yl)phenylmethanone and 11.6 g of sodium carbonate are suspended in 900 ml of dioxane, 900 ml of toluene and 400 ml of water. 4.2 g (3.6 mmol) of Pd(PPh3)4 are added to this suspension. The reaction mixture is heated under reflux for 7 h. After cooling, the precipitated solid is filtered off with suction and washed with water and ethanol and dried. The residue is extracted with hot toluene and recrystallised from toluene. Yield: 14.7 g (23 mmol), 70% of theory.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 7 h
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed with water and ethanol
  6. customdried
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised from toluene

Sources & evidence

ORD record
ord-dd1e8fa41ce348bfb08eea7acca2a6ea
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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