Water → 4-Chloro-6-(2,3-difluorobenzyl)pyrimidine

HRID 1592258

反応式

HRID 1592258 の反応式
[Cl-].C[SiH](C)C.[F:6][C:7]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9]Br.[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[CH:19][N:18]=1.O>O1CCCC1.BrC(Br)C.[Zn]>[Cl:16][C:17]1[CH:22]=[C:21]([CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[C:14]([F:15])[C:7]=2[F:6])[N:20]=[CH:19][N:18]=1

参加物

8

反応物 4

HCID 962WaterHCID 709434,6-DichloropyrimidineHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 131723440Tmsci

生成物 1

HCID 225997524-Chloro-6-(2,3-difluorobenzyl)pyrimidine収率 38.4%

試薬・触媒・溶媒 3

HCID 112011,1-Dibromoethane触媒HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

In 10 ml of tetrahydrofuran was suspended 1.3 g of zinc (powder), to which dibromoethane (2 drops) was added. The mixture was heated under reflux for 5 minutes, to which trimethylsilane chloride was added. The mixture was further heated under reflux for 5 minutes, to which a solution of 2.1 g of 2,3-difluorobenzyl bromide dissolved in 20 ml of tetrahydrofuran was slowly added with heating under reflux, followed by stirring for 20 minutes. (The solution thus obtained is referred to as solution G). In 10 ml of tetrahydrofuran were suspended 1.5 g of 4,6-dichloropyrimidine and 0.1 g of dichlorobistriphenylphosphine palladium, to which the above solution G was added, followed by heating under reflux for 3 hours and further stirring at room temperature for 12 hours. The reaction mixture was then poured into water and extracted three times with ethyl acetate. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.93 g of 4-chloro-6-(2,3-difluorobenzyl)pyrimidine.

後処理

  1. temperatureThe mixture was heated
  2. additionwas added
  3. temperatureThe mixture was further heated
  4. additionwas slowly added
  5. temperaturewith heating
  6. temperatureunder reflux
  7. custom(The solution thus obtained
  8. temperatureby heating
  9. temperatureunder reflux for 3 hours
  10. stirringfurther stirring at room temperature for 12 hours
  11. extractionextracted three times with ethyl acetate
  12. washwashed with water
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated

出典と根拠

ORDレコード
ord-95b6c9d84c6c4b7a947685dc16ad683e
出典データセット
uspto-grants-2007_11
特許番号
US07291730B2

関連ノート

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