1,2-Dichloroethane → 1-(4-Bromo-2-fluorophenyl)-3-chloro-1-propanone

HRID 520312ノート

反応式

HRID 520312 の反応式
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[C:8]([F:15])[CH:7]=1.[Cl:16][CH2:17][CH2:18]Cl>>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](=[O:11])[CH2:18][CH2:17][Cl:16])=[C:8]([F:15])[CH:7]=1

参加物

4

反応物 3

HCID 111,2-Dichloroethane2 回HCID 27340264-Bromo-2-fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 594738271-(4-Bromo-2-fluorophenyl)-3-chloro-1-propanone収率 68%

実験手順

To a stirred suspension of aluminum trichloride (153 g, 1.15 mol) in DCE (1000 mL) was added a solution of 144b (271 g, 1.14 mol) in DCE (1000 mL) at 0° C. See FIG. 3. Ethylene gas was bubbled through the dark suspension for 3 h until the acid chloride was consumed. The reaction mixture was then stirred at RT overnight, cooled to 0° C., and quenched with 4M HCl (500 mL). The organic phase was separated and washed with brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude residue was purified by column chromatography (PE/EA=30 to 10:1) to give 1-(4-bromo-2-fluorophenyl)-3-chloropropan-1-one 144c (210 g, 68%).

後処理

  1. customEthylene gas was bubbled through the dark suspension for 3 h until the acid chloride
  2. customwas consumed
  3. temperaturecooled to 0° C.
  4. customquenched with 4M HCl (500 mL)
  5. customThe organic phase was separated
  6. washwashed with brine (100 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by column chromatography (PE/EA=30 to 10:1)

出典と根拠

ORDレコード
ord-9946ceff88c245b994c6a22182dd4693
出典データセット
uspto-grants-2016_05
特許番号
US09326985B2

反応ノート

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