Pyrene, 1,6-Dibromo- → 1,6-Diisobutylpyrene

HRID 929276ノート

反応式

HRID 929276 の反応式
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH2:19](B(O)O)[CH:20]([CH3:22])[CH3:21].O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH2:19]([C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9]([CH2:4][CH:5]([CH3:16])[CH3:6])=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1)[CH:20]([CH3:22])[CH3:21]

参加物

7

反応物 3

HCID 176470Pyrene, 1,6-Dibromo-HCID 2734395(2-Methylpropyl)boronic acidHCID 22031701Potassium phosphate, tribasic, monohydrate

生成物 1

HCID 1237354951,6-Diisobutylpyrene収率 154.2%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒HCID 1140Toluene溶媒

実験手順

A mixture of 1,6-dibromopyrene (15.13 g, 42.0 mmol), isobutyl boronic acid (27.58 g, 270 mmol), potassium phosphate tribasic monohydrate (53.94 g, 254 mmol), Pd2(dba)3 (3.02 g, 3.30 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.00 g, 2.45 mmol) in toluene (300 mL) was fully degassing by bubbling through with nitrogen. The reaction mixture was maintained at reflux under nitrogen for 16 h. The reaction mixture was cooled, then filtered through a pad of Celite and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash chromatography using hexane to yield 1,6-diisobutylpyrene (10.18 g, 77% yield) as a white solid.

後処理

  1. customwas fully degassing
  2. customby bubbling through with nitrogen
  3. temperatureThe reaction mixture was maintained
  4. temperatureat reflux under nitrogen for 16 h
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered through a pad of Celite
  7. washwashed with toluene
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-6823bbaf959641f78a55b0d5ccdda25b
出典データセット
uspto-grants-2016_03
特許番号
US09293712B2

反応ノート

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