Benzene → HCID 86628499, compound

HRID 2242558Notes

Reaction equation

HRID 2242558 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>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.C(O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:14]2[C:19]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=3)=[CH:18][C:17]3[C:5]([CH3:10])([CH3:6])[C:17]4[C:16](=[CH:15][C:14]([C:8]5[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=5)=[C:19]([C:8]5[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=5)[CH:18]=4)[C:1]([CH3:3])([CH3:2])[C:16]=3[CH:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 27343204-tert-Butylphenylboronic acid

Product 1

HCID 86628499HCID 86628499, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

10 mmol of product in Example 2, 40 mmol of 4-tert-butylphenylboronic acid, and 0.2 mmol of Pd(PPh3)4 were charged in a reaction vessel under nitrogen. The mixture was added deoxygen benzene (50 mL), ethanol (4 mL), and 2M potassium carbonate solution (10 mL) to be dissolved, and then heated to 80° C. and reacted for 24 hours. The reaction result was extracted by 50 mL of ethyl acetate to obtain an organic layer. The organic layer was filtered through diatomite and dried by anhydrous magnesium sulphate. Most of the solvent of the dried organic layer was removed to obtain a solid. The solid was subsequently washed by distillation water, methanol, ethyl ether to obtain 2,3,6,7-Tetrakis-(4-tert-butyl-phenyl)-9,9,10,10-tetramethyl-9,10-dihydro-anthracene (hereinafter TTA-tBu). The Suzuki coupling was shown in Formula 7, and the product had spectra as below. 1H NMR (400 M Hz, CDCl3): δ 1.31 (s, 36 H), 1.79 (s, 12 H), 7.12 (d, 8 H, J=8.4 Hz), 7.24 (d, 8 H, J=8.4 Hz), 7.55 (s, 4 H). 13C NMR (100 M Hz, CDCl3): δ 31.4 (CH3), 34.4(C), 35.1 (CH3), 37.1 (C), 124.6 (CH), 128.9 (CH), 129.5 (CH), 138.3 (C), 138.8 (C), 141.0 (C), 149.1 (C). HRMS (FAB, m/z): calcd for C58H68 764.5321, found 765.5397 (M+H+). Anal. Calcd. for C58H68: C, 91.04; H, 8.96%. Found: C, 91.07; H, 8.90%. FIG. 4 shows UV-VIS absorption and photo luminescent spectra of the TTA-tBu in a dichloromethane solution and thin film type, and solid phosphorescence emission spectra at 77K of the TTA-tBu.

Workup

  1. dissolutionto be dissolved
  2. customreacted for 24 hours
  3. customThe reaction result
  4. extractionwas extracted by 50 mL of ethyl acetate
  5. customto obtain an organic layer
  6. filtrationThe organic layer was filtered through diatomite
  7. dry with materialdried by anhydrous magnesium sulphate
  8. customMost of the solvent of the dried organic layer was removed
  9. customto obtain a solid
  10. washThe solid was subsequently washed by distillation water, methanol, ethyl ether

Sources & evidence

ORD record
ord-f6f47138eebe4845b853b55549ca025c
Source dataset
uspto-grants-2010_03
Patent number
US07671241B2

Reaction notes

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