Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 66790679, compound

HRID 1664094Notes

Reaction equation

HRID 1664094 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].Br[C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>[Zn].C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:6]

Participants

5

Reactant 2

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 76403Benzoyl chloride, 3,4-dichloro-

Product 1

HCID 66790679HCID 66790679, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture comprising 10.0 g of 3,4-dichlorobenzoyl chloride, 9.31 g of ethyl 2-bromoisobutyrate and 90 ml of anhydrous diethyl ether, was dropwise added to 3.12 g of zinc in a nitrogen atmosphere, followed by a reaction for 15 hours under reflux. The reaction mixture was filtered through celite, and the filtrate was washed with 20% sulfuric acid and then with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/19) to obtain 8.7 g of oily ethyl 2-(3′,4′-dichlorobenzoyl)isobutyrate. The NMR spectrum data of this product is as follows.

Workup

  1. customfollowed by a reaction for 15 hours
  2. temperatureunder reflux
  3. filtrationThe reaction mixture was filtered through celite
  4. washthe filtrate was washed with 20% sulfuric acid
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/19)

Sources & evidence

ORD record
ord-9e0883f571f34aaca82db3250974e00e
Source dataset
uspto-grants-2011_10
Patent number
US08039420B2

Reaction notes

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