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Sulfuric Acid → Diethyl (2,3-dichloro-4,5-difluorobenzoyl)propanedioate

HRID 2232632
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HRID 2232632 반응식
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:13][C:14]1[C:22]([Cl:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:15]=1[C:16](Cl)=[O:17].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C(O)C.C(Cl)(Cl)(Cl)Cl>[Cl:13][C:14]1[C:22]([Cl:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:15]=1[C:16]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 10999320Benzoyl chloride, 2,3-dichloro-4,5-difluoro-

생성물 1

HCID 14071801Diethyl (2,3-dichloro-4,5-difluorobenzoyl)propanedioate수율 107.3%

시약·촉매·용매 3

HCID 702Ethanol
용매
2회
HCID 1140Toluene용매2회
HCID 5943Carbon Tetrachloride용매

실험 절차

Magnesium turnings (0.77 g) and carbon tetrachloride (0.4 ml) was added to absolute ethanol (5.3 ml). To the stirring suspension was added a solution of diethyl malonate (4.89 g) and absolute ethanol (8.5 ml) in toluene (21.3 ml) dropwise during 40 minutes at 20° to 40° C. The mixture was stirred at 50° to 60° C. for 2 hours, and then cooled in an acetone-dry ice bath. A solution of 2,3-dichloro-4,5-difluorobenzoyl chloride (6.00 g) in anhydrous toluene (7.1 ml) was added dropwise to the resulting solution at -18° to -13° C. during 10 minutes. The mixture was warmed gradually to room temperature during 2 hours and then mixed with ice water (17 ml) containing concentrated sulfuric acid (1.1 ml). The resulting organic layer was collected and the water layer was extracted with toluene. The combined organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated to give the title compound (9.68 g) as pale yellow oil.

후처리

  1. temperaturecooled in an acetone-dry ice bath
  2. customThe resulting organic layer was collected
  3. extractionthe water layer was extracted with toluene
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bf7c0540b87742ffbc083bbae5ab2b3d
출처 데이터셋
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04788320

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