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Hydrogen Peroxide → 4-Cyano-3,5-difluoro-4'-methoxybiphenyl

HRID 466486
ノート
印刷プレビュー

反応式

HRID 466486 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]=[C:19]([F:21])[C:16]([C:17]#[N:18])=[C:15]([F:22])[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[C:19]([F:21])=[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:22])#[N:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 27569164-Bromo-2,6-difluorobenzonitrile

生成物 1

HCID 150656534-Cyano-3,5-difluoro-4'-methoxybiphenyl

試薬・触媒・溶媒 3

HCID 11979704
Tetrakis(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 (11.50 g, 0.076 mol) in ethanol (90 ml) was added dropwise to a stirred mixture of compound 7 (15.0 g, 0.069 mol) and tetrakis(triphenylphosphine)palladium(O) (2.38 g, 2.06 mmol) in benzene (130 ml) and 2M-sodium carbonate (100 ml) at room temperature under dry nitrogen. The stirred mixture was heated under reflux (90°-95° C.) for 4.5 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 further cooled to 2° C., and the product was filtered off and washed with water. The product was dried (CaCl2) in vacuo to give fawn-coloured needles.

後処理

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux (90°-95° C.) for 4.5 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 fawn-coloured needles

出典と根拠

ORDレコード
ord-a9b3fef8eaeb466b88be348719a3b928
出典データセット
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05156763

反応ノート

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