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4-(Trimethylsilyl)phenylboronic Acid (contains varying amounts of Anhydride) → 1,3,6,8-Tetrakis-(4-trimethylsilyl-phenyl)-pyrene

HRID 1767299
ノート
印刷プレビュー

反応式

HRID 1767299 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

HCID 211135601,3,6,8-Tetrakis-(4-trimethylsilyl-phenyl)-pyrene

試薬・触媒・溶媒 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-abc5c4ba36814a2eb15590e146133a7e
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07233019B2

反応ノート

読み込み中…

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