Acetyl chloride → 1-[2-Methoxy-5-(pentafluoroethyl)phenyl]ethanone

HRID 504059ノート

反応式

HRID 504059 の反応式
[Li]CCCC.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.[C:21](Cl)(=[O:23])[CH3:22]>CCCCCC.C1COCC1.CCOCC.[Cl-].[Zn+2].[Cl-]>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([F:19])([F:20])[C:15]([F:16])([F:17])[F:18])=[CH:12][C:13]=1[C:21](=[O:23])[CH3:22]

参加物

8

反応物 3

HCID 6367Acetyl chlorideHCID 128719661-Methoxy-4-(pentafluoroethyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 860887051-[2-Methoxy-5-(pentafluoroethyl)phenyl]ethanone

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

7.4 ml of BuLi at 2.5M in hexane are added, at −70° C., to a solution of 3.5 g of 1-methoxy-4-pentafluoroethylbenzene in 50 ml of anhydrous THF. The medium is stirred for 30 minutes at −70° C. and then for 45 minutes at 0° C. 15.5 ml of a 1M solution of zinc chloride in ether are then added. After stirring for 10 minutes at 0° C., 1.33 ml of acetyl chloride are added. The medium is then deoxygenated with nitrogen and 332 mg of benzyl(chloro)bis(triphenylphosphine)palladium in 5 ml of anhydrous THF are introduced. The medium is stirred for 2 hours 30 minutes at 0° C. and then for 72 hours at RT. The medium is poured onto 2.5M HCl solution and then extracted with ether. The organic phase is washed with 5% NaHCO3 in water, with water and then with saturated NaCl solution. After drying over MgSO4 and evaporation, the crude product is purifed by flash chromatography on silica to give 2.25 g of a white solid. m.p.=47° C.

後処理

  1. waitfor 45 minutes at 0° C
  2. stirringAfter stirring for 10 minutes at 0° C.
  3. customThe medium is then deoxygenated with nitrogen and 332 mg of benzyl(chloro)bis(triphenylphosphine)palladium in 5 ml of anhydrous THF
  4. additionare introduced
  5. stirringThe medium is stirred for 2 hours 30 minutes at 0° C.
  6. waitfor 72 hours at RT
  7. additionThe medium is poured onto 2.5M HCl solution
  8. extractionextracted with ether
  9. washThe organic phase is washed with 5% NaHCO3 in water, with water
  10. dry with materialAfter drying over MgSO4 and evaporation

出典と根拠

ORDレコード
ord-3470a3f5deaf4aaaa4a0844b60602a50
出典データセット
uspto-grants-2010_08
特許番号
US07777041B2

反応ノート

読み込み中…