Ethyl 2-(3,4-difluorophenyl)-2-oxoacetate → Ethyl 3,3',4,4'-tetrafluorobenzilate

HRID 2099338Notes

Reaction equation

HRID 2099338 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[C:9]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[C:7]([F:8])[CH:6]=1)([OH:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

3

Reactant 1

HCID 2774352Ethyl 2-(3,4-difluorophenyl)-2-oxoacetate

Product 1

HCID 11163248Ethyl 3,3',4,4'-tetrafluorobenzilate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

The Grignard reagent is prepared from 2.24 g (0.092 mol) of magnesium chips, a few granules of iodine, and 17.80 g (0.092 mol) of 1-bromo-3,4-difluorobenzene in 100 mL of THF at 50° C. After the halide has all been added, the mixture is stirred for another hour. The Grignard reagent thus obtained is added dropwise to 18.81 g (0.088 mol) of ethyl 3,4-difluorophenylglyoxylate in 80 mL of THF at 10° C.-15° C. and the mixture obtained is stirred for 2 hours at 5° C. The white suspension is poured onto ice/sulfuric acid for working up, extracted with ethyl acetate, the organic phase is washed with water, dried over MgSO4, and evaporated to dryness. The crude product is purified by column chromatography (eluent: toluene). Yield: 10.80 g of oil 4.1. (38% of theory).

Workup

  1. customthe mixture obtained
  2. additionThe white suspension is poured onto ice/sulfuric acid
  3. extractionextracted with ethyl acetate
  4. washthe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe crude product is purified by column chromatography (eluent: toluene)

Sources & evidence

ORD record
ord-dd5cbe883cc34276af2bbf8531884580
Source dataset
uspto-grants-2009_08
Patent number
US07569581B2

Reaction notes

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