1-Bromo-2-chlorobenzene → 5-(4-Chlorophenoxy)-2-methylpyridine

HRID 903852ノート

反応式

HRID 903852 の反応式
[K].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17]>CN(C)C=O.CO.[Cu]>[Cl:17][C:12]1[CH:13]=[CH:14][C:15]([O:2][C:3]2[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=2)=[CH:16][CH:11]=1

参加物

7

反応物 3

HCID 127541-Bromo-2-chlorobenzeneHCID 142752-Methyl-5-hydroxypyridineHCID 5462222Potassium

生成物 1

HCID 233352855-(4-Chlorophenoxy)-2-methylpyridine

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

7.35 g of a potassium salt of 5-hydroxy-2-methylpyridine was suspended in 20 ml of dimethylformamide, and 9.6 g of bromochlorobenzene and 800 mg of a copper powder were added to the suspension. The reaction was effected at a temperature of 120° C. for a period of 18 hours in a nitrogen stream while stirring. After allowing the reaction mixture to cool, the reaction mixture was diluted with 50 ml of methanol and then filtered. The filtrate was immediately concentrated to dryness, and 200 ml of chloroform and 100 ml of water were added to the dried material, and the mixture adjusted to a pH of 9 with 5 N sodium hydroxide. The insoluble matter was again separated by filtration. The resulting chloroform layer was dried with anhydrous sodium sulfate and immediately concentrated to dryness to obtain 8.2 g of oily 5-(p-chlorophenoxy)-2-methylpyridine. Gas chromatography revealed that the thus-obtained product contained no 5-(p-bromophenoxy)-2-methylpyridine.

後処理

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationThe filtrate was immediately concentrated to dryness, and 200 ml of chloroform and 100 ml of water
  4. additionwere added to the dried material
  5. customThe insoluble matter was again separated by filtration
  6. dry with materialThe resulting chloroform layer was dried with anhydrous sodium sulfate
  7. concentrationimmediately concentrated to dryness

出典と根拠

ORDレコード
ord-59acbd61fd454b489c54afc81051f46e
出典データセット
uspto-grants-1980_10
特許番号
US04229448

反応ノート

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