Hydrogen Peroxide → 2-fluoro-4-(4-methoxyphenyl)benzonitrile

HRID 466483ノート

反応式

HRID 466483 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([F:21])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].OO>C(O)C.C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:14][C:15]=1[F:21])#[N:18]

参加物

8

反応物 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 7360294-Bromo-2-fluorobenzonitrile

生成物 1

HCID 27633572-fluoro-4-(4-methoxyphenyl)benzonitrile

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 241Benzene溶媒HCID 702Ethanol溶媒

反応条件

温度
2 °C

実験手順

A solution of compound 1 (10.64 g, 0.07 mol) in ethanol (90 ml) was added dropwise to a stirred mixture of compound 3 (12.0 g, 0.06 mol) and tetrakis(triphenylphosphine)palladium(O) (2.10 g, 1.82 mmol) in benzene (125 ml) and 2M-sodium carbonate (100 ml) at room temperature under dry nitrogen. The stirred mixture was heated under reflux (90°-95° C.) for 2.5 h (i.e., until glc analysis revealed absence of starting material). The mixture was cooled and stirred for 1 h at room temperature with 30% hydrogen peroxide (2 ml). The mixture was cooled further to 2° C., the product was filtered off and washed with water. The product was dried (CaCl2) in vacuo to give a yellow powder.

後処理

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux (90°-95° C.) for 2.5 h (i.e., until glc analysis revealed absence of starting material)
  3. temperatureThe mixture was cooled
  4. filtrationthe product was filtered off
  5. washwashed with water
  6. dry with materialThe product was dried (CaCl2) in vacuo
  7. customto give a yellow powder

出典と根拠

ORDレコード
ord-b54d637471d4469b89e7e20e7568fcc3
出典データセット
uspto-grants-1992_10
特許番号
US05156763

反応ノート

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