ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

N,N,N',N'-Tetramethylethylenediamine → 4-Acetyl-2-fluorobenzonitrile

HRID 500133
ノート
印刷プレビュー

反応式

HRID 500133 の反応式
C[N:2](C)[CH2:3][CH2:4]N(C)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.BrC1[CH:57]=[CH:56][C:55]([C:58](=[O:60])[CH3:59])=[CH:54][C:53]=1[F:61]>CN(C)C=O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:58]([C:55]1[CH:56]=[CH:57][C:4]([C:3]#[N:2])=[C:53]([F:61])[CH:54]=1)(=[O:60])[CH3:59]
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

7

反応物 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 228319141-(4-Bromo-3-fluorophenyl)ethan-1-one

生成物 1

HCID 224816534-Acetyl-2-fluorobenzonitrile

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

N,N,N′,N′-Tetramethylethylenediamine (0.667 mL, 4.42 mmol), zinc cyanide (1.46 g, 12.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (54.05 mg, 0.059 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (124.3 mg, 0.215 mmol) was added successively to a solution of 1-(4-bromo-3-fluorophenyl)ethanone (4.34 g, 20.0 mmol) in N,N-dimethylformamide (15 mL) in a microwave tube. The tube was sealed and degassed three times, and heated to 160° C. under microwave irradiation with a 240 s hold time, and 300 Watt maximum power input. After cooling, the reaction mixture was filtered through a pad of Celite with a thin layer of silica gel in the middle using dichloromethane as the eluant. The combined filtrates were concentrated under reduced pressure. The residue was purified by chromatography on silica gel with ethyl acetate in hexanes (0-40%) to give the desired product. (3.20 g, 98.1%).

後処理

  1. customThe tube was sealed
  2. customdegassed three times
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through a pad of Celite with a thin layer of silica gel in the middle
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel with ethyl acetate in hexanes (0-40%)

出典と根拠

ORDレコード
ord-77ff4e5b5c7244ae8e31d1c30552ca0c
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07767675B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート