4-(Trimethylsilyl)phenylboronic Acid (contains varying amounts of Anhydride) → HCID 21113560, compound

HRID 1767299Notes

Reaction equation

HRID 1767299 reaction equation
Cl[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[C:11](Cl)=[CH:10][C:9](Cl)=[C:8]4[CH:7]=[CH:6][C:5]3=[C:4](Cl)[CH:3]=1.[CH3:21][Si:22]([CH3:33])([CH3:32])[C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(P(C(C)(C)C)[CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH3:21][Si:22]([CH3:33])([CH3:32])[C:23]1[CH:28]=[CH:27][C:26]([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[C:11]([C:26]3[CH:27]=[CH:28][C:23]([Si:22]([CH3:33])([CH3:32])[CH3:21])=[CH:24][CH:25]=3)=[CH:10][C:9]([C:26]3[CH:27]=[CH:28][C:23]([Si:22]([CH3:33])([CH3:32])[CH3:21])=[CH:24][CH:25]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[C:4]([C:2]3[CH:15]=[CH:14][C:39]([Si:40]([CH3:42])([CH3:41])[CH3:43])=[CH:4][CH:3]=3)[CH:3]=2)=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 17104-(Trimethylsilyl)phenylboronic Acid (contains varying amounts of Anhydride)HCID 10796Cesium carbonateHCID 66473Pyrene, 1,3,6,8-tetrachloro-HCID 12583313Di-tert-butyl-trimethylsilylmethyl-phosphane

Product 1

HCID 21113560HCID 21113560, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1,3,6,8-Tetrachloro-pyrene (3.50 g, 0.0103 mol), 4-trimethylsilylphenylboronic acid (10.0 g, 0.0515 mol), tris(dibenzylideneacetone)dipalladium(0) (1.18 g, 0.00129 mol), di-tert-butyl-trimethylsilylmethyl-phosphane (0.72 g, 0.0031 mol), cesium carbonate (16.78 g, 0.0515 mol) and dioxane (100 ml) were stirred at room temperature for 24 hours. The resultant mixture was poured into 200 ml of water and extracted twice with 200 ml of methylene chloride. The organic phase was dried over magnesium sulfate overnight and filtered. The solvent was removed on a roto-evaporator and the residue was purified by chromatography on silica gel with petroleum ether/ethyl ether (10/0.5) as eluent. Yield of 1,3,6,8-tetrakis-(4-trimethylsilanyl-phenyl)-pyrene was 2.39 g (29.11%) as a yellow solid with no m.p. below 250° C. 1H NMR (CD2Cl2) 0.15 (s., 36H, Me), 7.40–7.60 (br., 22H, arom-H), 7.91 (s., 2H, arom.-H), 8.20 (s., 4H, arom.-H). LC/MS: exact mass calculated for C52H58Si4: 794.36. Found: 794.36. The structure was confirmed by X-ray analysis.

Workup

  1. extractionextracted twice with 200 ml of methylene chloride
  2. dry with materialThe organic phase was dried over magnesium sulfate overnight
  3. filtrationfiltered
  4. customThe solvent was removed on a roto-evaporator
  5. customthe residue was purified by chromatography on silica gel with petroleum ether/ethyl ether (10/0.5) as eluent

Sources & evidence

ORD record
ord-abc5c4ba36814a2eb15590e146133a7e
Source dataset
uspto-grants-2007_06
Patent number
US07233019B2

Reaction notes

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