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1-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone → 3-Acetyl-5-chloro-2-hydroxy-6-methylbenzonitrile

HRID 1499721
ノート
印刷プレビュー

反応式

HRID 1499721 の反応式
Br[C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[Cu](C#N)[C:15]#[N:16]>CN1CCCC1=O.CCOC(C)=O.Cl>[C:10]([C:4]1[C:3]([OH:13])=[C:2]([C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=1)[C:15]#[N:16])(=[O:12])[CH3:11]
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 120274791-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanoneHCID 178418260HCID 178418260、化合物

生成物 1

HCID 583685163-Acetyl-5-chloro-2-hydroxy-6-methylbenzonitrile

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone
溶媒

反応条件

温度
200 °C

実験手順

A mixture of 1-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone (4.85 g, 18.4 mmol) and copper cyanide (2.47 g, 27.6 mmol) in N-methylpyrrolidinone (15 mL) was heated at 200° C. for 1 h. After cooled to rt, the mixture was diluted with EtOAc and 1 N HCl. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, then brine and dried over magnesium sulfate, then concentrated to dry under reduced pressure. The residue was used directly in next step (3.7 g, 96%). LCMS calculated for C10H9ClNO2 (M+H)+: m/z=210.0; Found: 210.1.

後処理

  1. temperatureAfter cooled to rt
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialbrine and dried over magnesium sulfate
  6. concentrationconcentrated
  7. customto dry under reduced pressure

出典と根拠

ORDレコード
ord-e8510ea7f3e140e1aaafa95a34f28f58
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09199982B2

反応ノート

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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