Sulfuric Acid → Diethyl 3-bromo-2,4,5-trifluorobenzoylmalonate

HRID 1761649노트

반응식

HRID 1761649 반응식
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br:13][C:14]1[C:15]([F:25])=[C:16]([CH:20]=[C:21]([F:24])[C:22]=1[F:23])[C:17](Cl)=[O:18].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C(O)C.C(Cl)(Cl)(Cl)Cl>[Br:13][C:14]1[C:15]([F:25])=[C:16]([CH:20]=[C:21]([F:24])[C:22]=1[F:23])[C:17]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:18]

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 137488023-Bromo-2,4,5-trifluorobenzoyl chloride

생성물 1

HCID 13748803Diethyl 3-bromo-2,4,5-trifluorobenzoylmalonate수율 98.6%

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 1140Toluene용매2회HCID 5943Carbon Tetrachloride용매

실험 절차

Magnesium turnings (0.22 g) and carbon tetrachloride (0.1 ml) was added to absolute ethanol (1.5 ml). To the stirring suspension was added dropwise a solution of diethyl malonate (1.4 g) and absolute ethanol (2 ml) in toluene (6 ml) during 25 minutes at 50°-60° C. The mixture was stirred for 40 minutes, and then cooled. A solution of 3-bromo-2,4,5-trifluorobenzoyl chloride (2.27 g) in anhydrous toluene (3 ml) was added dropwise to the solution at -8°~-4.5° C. during 28 minutes. The mixture was stirred for 2 hours and then mixed with ice-chilled diluted sulfuric acid. The resulting organic layer was collected and the water layer was extracted with toluene (6 ml×4). The combined organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated to give the title compound (3.25 g) as pale yellow oil.

후처리

  1. temperaturecooled
  2. stirringThe mixture was stirred for 2 hours
  3. additionmixed with ice-
  4. customThe resulting organic layer was collected
  5. extractionthe water layer was extracted with toluene (6 ml×4)
  6. washThe combined organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-45a5c435ce104f1bb8ff9f474d80d3b9
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04826982

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