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3,5-Dibromopicolinonitrile → 3-Bromo-5-(2,6-dichlorobenzyl)picolinonitrile

HRID 535897
ノート
印刷プレビュー

反応式

HRID 535897 の反応式
[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](Br)[CH:7]=1.[Cl-].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:14]=1[CH2:15][Zn+]>O1CCCC1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([CH2:15][C:14]2[C:13]([Cl:12])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:21])[CH:7]=1
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

6

反応物 2

HCID 123612023,5-DibromopicolinonitrileHCID 178478101HCID 178478101、化合物

生成物 1

HCID 704976733-Bromo-5-(2,6-dichlorobenzyl)picolinonitrile

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
85 °C

実験手順

A solution of the product of EXAMPLE 1A (4.52 g, 15.34 mmol) in tetrahydrofuran (75 mL) was treated with palladium tetrakis(triphenylphosphine) (0.887 g, 0767 mmol) and 2,6-dichlorobenzyl zinc chloride (46 mL, 0.5M in tetrahydrofuran). The mixture was heated at 85° C. for 1 hour. After cooling to ambient temperature, the mixture was diluted with water and extracted with ethyl acetate. The organics were washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. Purification by silica gel chromatography (0-100% ethyl acetate in hexanes) provided the title compound. MS (LC-MS) m/z 342 (M+H)+.

後処理

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel chromatography (0-100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-ce8af1ac7929407fbff41c9d0f21dc29
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859546B2

反応ノート

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