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

HRID 899039Notes

Reaction equation

HRID 899039 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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 vacuo 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%).

Workup

  1. customAfter removal of volatiles in vacuo 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

Sources & evidence

ORD record
ord-915860453d454cc0b07c2804b595be54
Source dataset
uspto-grants-2008_04
Patent number
US07354916B2

Reaction notes

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