Triphenylphosphine → 2'-Acetyl[1,1'-biphenyl]-4-carbonitrile

HRID 270621

반응식

HRID 270621 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O)(=[O:22])[CH3:21].O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:42]1[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:42]1[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=1)(=[O:22])[CH3:21]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 121634-ChlorobenzonitrileHCID 27343092-Acetylphenylboronic acidHCID 22031701Potassium phosphate, tribasic, monohydrate

생성물 1

HCID 121884252'-Acetyl[1,1'-biphenyl]-4-carbonitrile

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

Bis(triphenylphosphine)palladium dichloride (PdCl2(PPh3)2) (0.6 g, 0.86 mmol), triphenylphosphine (0.44 g, 1.74 mmol), (2-acetylphenyl)boronic acid (6 g, 3.76 mmol) and tripotassium phosphate hydrate (16 g, 7.54 mmol) were placed in a flask. Nitrogen was blown into the flask and then the flask was filled with toluene (40 ml) and 4-chlorbenzonitrile (4 g, 2.90 mmol). The reaction mixture was stirred at 80° C. for 4 hours. The reaction mixture was cooled and washed with water. The organic layer was dried over sodium sulfate and then the solvent was evaporated. The product, 2′-acetyl-4-biphenylcarbonitrile (5a) was purified by a column (hexane/ethyl acetate=8/1). Yield: 3.3 g (51%).

후처리

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated
  5. customThe product, 2′-acetyl-4-biphenylcarbonitrile (5a) was purified by a column (hexane/ethyl acetate=8/1)

출처 및 근거

ORD 기록
ord-6a8ed67d0e5942ddaf4af41eeb0a8c3e
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449574B2

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