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

HRID 270621

反応式

HRID 270621 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-6a8ed67d0e5942ddaf4af41eeb0a8c3e
出典データセット
uspto-grants-2008_11
特許番号
US07449574B2

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