Hydrochloric Acid → Diethyl (2,6-Dichloro-4-fluoro-phenyl)-malonate

HRID 1066034ノート

反応式

HRID 1066034 の反応式
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Br[C:15]1[C:20]([Cl:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=1[Cl:23].Cl>[Cu]Br.O1CCOCC1>[Cl:21][C:20]1[CH:19]=[C:18]([F:22])[CH:17]=[C:16]([Cl:23])[C:15]=1[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 211981432-Bromo-1,3-dichloro-5-fluorobenzene

生成物 1

HCID 15510255Diethyl (2,6-Dichloro-4-fluoro-phenyl)-malonate収率 54.5%

試薬・触媒・溶媒 2

HCID 24593copper(I) bromide触媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
55 °C

実験手順

Diethyl malonate (0.49 mol) is added to a mixture of sodium hydride (0.51 mol) and 1,4-dioxane (140 ml) at 55 to 60° C. within 2 hours. The mixture is stirred for 10 minutes at 55° C. and copper(I) bromide (0.05 mol) is added. After 15 minutes a mixture of 1-bromo-2,6-dichloro-4-fluoro-benzene (0.25 mol) and 1,4-dioxane (10 ml) is added. The reaction mixture is heated at 100° C. for 15 hours and cooled to 15° C. Hydrochloric acid (12N, 35 ml) is added slowly at 15 to 20° C. The precipitate is filtered off. The filtrate is extracted with diethylether. The organic phase is separated, dried with anhydrous sodium sulphate and filtered. The filtrate is evaporated under reduced pressure to yield 44 g of the product as yellow crystals having a melting point of 170° C.

後処理

  1. additionis added
  2. temperatureThe reaction mixture is heated at 100° C. for 15 hours
  3. temperaturecooled to 15° C
  4. filtrationThe precipitate is filtered off
  5. extractionThe filtrate is extracted with diethylether
  6. customThe organic phase is separated
  7. dry with materialdried with anhydrous sodium sulphate
  8. filtrationfiltered
  9. customThe filtrate is evaporated under reduced pressure

出典と根拠

ORDレコード
ord-293b5934e6b74932b22467f60352c185
出典データセット
uspto-grants-2001_06
特許番号
US06242451B1

反応ノート

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