Toluene → 4'-Formyl-3'-(trifluoromethyl)biphenyl-2-carbonitrile

HRID 519498노트

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HRID 519498 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1OB(O)O)#[N:15].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:17]2[C:16]([C:14]#[N:15])=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:3][C:4]=1[C:10]([F:13])([F:12])[F:11])=[O:7]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 121872184-Bromo-2-(trifluoromethyl)benzaldehydeHCID 217080892-Cyano-phenylboric acid

생성물 1

HCID 866440264'-Formyl-3'-(trifluoromethyl)biphenyl-2-carbonitrile수율 32.7%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of 4-bromo-2-(trifluoromethyl)benzaldehyde (9 g), 2-cyano-phenylboric acid (9.5 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (2.9 g), tetrabutylammonium bromide (1.15 g), 2M aqueous sodium carbonate solution (30 mL) and toluene (100 mL) was stirred at 100° C. overnight under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 32%).

후처리

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-c9feda5c388842dfb335337ba5cd470b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115136B2

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