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

HRID 929276노트

반응식

HRID 929276 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

HCID 1237354951,6-Diisobutylpyrene수율 154.2%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6823bbaf959641f78a55b0d5ccdda25b
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09293712B2

반응 노트

불러오는 중…