Cesium carbonate → HCID 21113559, compound

HRID 1767300Notes

Reaction equation

HRID 1767300 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:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=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:24]=[C:25]([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[C:11]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([Si:22]([CH3:33])([CH3:32])[CH3:21])[CH:24]=3)=[CH:10][C:9]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([Si:22]([CH3:33])([CH3:32])[CH3:21])[CH:24]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[C:4]([C:3]3[CH:2]=[CH:15][CH:14]=[C:39]([Si:40]([CH3:42])([CH3:41])[CH3:43])[CH:4]=3)[CH:3]=2)[CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 66473Pyrene, 1,3,6,8-tetrachloro-HCID 45771813-(Trimethylsilyl)phenylboronic acidHCID 12583313Di-tert-butyl-trimethylsilylmethyl-phosphane

Product 1

HCID 21113559HCID 21113559, compound

Reagents, catalysts & solvents 3

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

Procedure

1,3,6,8-Tetrachloro-pyrene (4.38 g, 0.0129 mol), 3-trimethylsilylphenylboronic acid (15.0 g, 0.0773 mol), tris(dibenzylideneacetone)dipalladium(0) (1.77 g, 0.00193 mol), di-tert-butyl-trimethylsilylmethyl-phosphane (1.08 g, 0.0047 mol), cesium carbonate (25.17 g, 0.0773 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 using petroleum ether/ethyl ether (10/0.5) as eluent. Yield of 1,3,6,8-tetrakis-(3-trimethylsilyl-phenyl)-pyrene was 1.30 g (12.68%) as a yellow solid with no m.p. below 250° C. 1H NMR (CD2Cl2) 0.20 (s., 36H, Me), 7.40–8.20 (br., 28H, arom-H). LC/MS: exact mass calculated for C52H58Si4: 794.36. Found: 794.36.

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

Sources & evidence

ORD record
ord-b6bf328bec454c35aa0d1fb50964e5e3
Source dataset
uspto-grants-2007_06
Patent number
US07233019B2

Reaction notes

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