2,3,4,5-Tetrafluorobenzoyl chloride → Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

HRID 130315

반응식

HRID 130315 반응식
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([O-:5])=O.[K+].[Mg+2].[Cl-].[Cl-].[F:14][C:15]1[C:23]([F:24])=[C:22]([F:25])[C:21]([F:26])=[CH:20][C:16]=1C(Cl)=O>C(#N)C>[CH2:8]([O:7][C:1](=[O:6])[CH2:2][C:3](=[O:5])[C:20]1[CH:16]=[C:15]([F:14])[C:23]([F:24])=[C:22]([F:25])[C:21]=1[F:26])[CH3:9]

참가 물질

5

반응물 3

HCID 27336892,3,4,5-Tetrafluorobenzoyl chlorideHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium Chloride

생성물 1

HCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

Potassium ethyl malonate (3.66 g, 21.5 mmol), MgCl2 (2.44 g, 25.7 mmol) and TEA (2.05 g, 20.3 mmol) were mixed in acetonitrile (70 ml) at 10-15° C. for 2.5 hr. 2,3,4,5-tetrafluorobenzoyl chloride (2.00 g, 10.3 mmol) in acetonitrile (10 ml) was added at 0° C. over 15 min followed by a second addition of TEA (0.23 g, 2.3 mmol). After allowing to warm to RT, the mixture was stirred for 16 hr. After removal of volatiles in vacculo Toluene (30 ml) was added and removed in vacuo. Following the addition of toluene (60 ml), HCl 1.5 M (40 ml) was added cautiously, ensuring the temperature did not exceed 25° C. The organic fraction was washed with HCl 1.5 M (2×25 ml) and water (2×25 ml), dried over MgSO4 and reduced to a light orange oil in vacuo ([M+1]+265, 98%).

후처리

  1. customAfter removal of volatiles in vacculo Toluene (30 ml)
  2. additionwas added
  3. customremoved in vacuo
  4. additionthe addition of toluene (60 ml), HCl 1.5 M (40 ml)
  5. additionwas added cautiously
  6. customdid not exceed 25° C
  7. washThe organic fraction was washed with HCl 1.5 M (2×25 ml) and water (2×25 ml)
  8. dry with materialdried over MgSO4

출처 및 근거

ORD 기록
ord-474bceeecd274ea987153a50a8377102
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381720B2

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