Ethanol → 2,3,4,6-Tetrafluorobenzoic acid ethyl ester

HRID 729358ノート

反応式

HRID 729358 の反応式
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[C:7]([F:13])[C:3]=1[C:4]([OH:6])=[O:5].[C:14](Cl)(=O)[C:15](Cl)=O.C(O)C.C([O-])(O)=O.[Na+]>ClCCl.CN(C)C=O.C1C=CC=CC=1>[CH2:14]([O:5][C:4](=[O:6])[C:3]1[C:7]([F:13])=[CH:8][C:9]([F:12])=[C:10]([F:11])[C:2]=1[F:1])[CH3:15]

参加物

8

反応物 4

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 27765912,3,4,6-tetrafluorobenzoic Acid

生成物 1

HCID 210411752,3,4,6-Tetrafluorobenzoic acid ethyl ester収率 60.1%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 241Benzene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

2,3,4,6-Tetrafluorobenzoic acid (4.8 g, 24.7 mmol) in dichloromethane (80 mL) is cooled to 0° C. under a nitrogen atmosphere and treated with oxalyl chloride (11.2 mL, 128 mmol) followed by anhydrous N,N-dimethylformamide (2 drops). The mixture is warmed to room temperature and stirred for 2 hours. The solution is co-evaporated with benzene to yield an oil that is taken up in dichloromethane (80 mL), cooled to 0° C. under an inert atmosphere, and treated with anhydrous ethanol (15 mL, 258 mmol). After 5 hours at room temperature, the solution is poured into saturated NaHCO3 and extracted with chloroform. The organic phase is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to provide the title compound (3.3 g). This material is used without further purification. 1H NMR (CDCl3): δ 6.93-6.75 (m, 1H), 4.42 (q, 2H), 1.39 (t, 3H).

後処理

  1. customto yield an oil that
  2. temperaturecooled to 0° C. under an inert atmosphere
  3. waitAfter 5 hours at room temperature
  4. extractionextracted with chloroform
  5. washThe organic phase is washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-3b35c986c6404776ae92641734cd98ea
出典データセット
uspto-grants-2009_09
特許番号
US07582627B2

反応ノート

読み込み中…