Toluene → 2,5-Diphenyl-4-ethylpyridine

HRID 1897977노트

반응식

HRID 1897977 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[CH:16]=[C:15]([CH2:17][CH3:18])[C:14](I)=[CH:13][N:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:28]1(C)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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.O>[C:1]1([C:11]2[CH:16]=[C:15]([CH2:17][CH3:18])[C:14]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:13][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 582007282-Chloro-4-ethyl-5-iodopyridine

생성물 1

HCID 584350442,5-Diphenyl-4-ethylpyridine수율 90.9%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 962Water용매

실험 절차

Phenylboronic acid (11.0 g, 90 mmol), 2-chloro-4-ethyl-5-iodopyridine (8.00 g, 30 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (492 mg, 1.2 mmol), and potassium phosphate tribasic (20.7 g, 90 mmol), 250 ml, of toluene and 25 mL of water were placed in a 1 L round-bottom flask. Nitrogen was bubbled directly into the mixture for 30 min after which tris(dibenzylideneacetone)dipalladium(0) (275 mg, 0.3 mmol) was added. Nitrogen was bubbled for another 15 min, then the reaction mixture was heated to reflux for 16 h under nitrogen. After the reaction was completed the mixture was cooled and the organic layer was separated from the aqueous layer. The organic layer was washed with saturated brine solution and dried over magnesium sulfate. The solution was filtered and the solvent was removed under vacuum to give a off-white solid. This crude was purified by silica gel column chromatography eluting with 10% ethyl acetate/hexanes. 7.0 g of desired product was obtained after purification (90.9% yield).

후처리

  1. additionwas added
  2. customNitrogen was bubbled for another 15 min
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 16 h under nitrogen
  5. temperaturewas cooled
  6. customthe organic layer was separated from the aqueous layer
  7. washThe organic layer was washed with saturated brine solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe solution was filtered
  10. customthe solvent was removed under vacuum
  11. customto give a off-white solid
  12. customThis crude was purified by silica gel column chromatography
  13. washeluting with 10% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-afc643553f3143d19b431b6b4132882f
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519384B2

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