Ethyl Acetate → HCID 58306846, compound

HRID 1909864Notes

Reaction equation

HRID 1909864 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[Br:16]N1C(=O)CCC1=O.C(OCC)(=O)C>N(C(C)(C)C#N)=NC(C)(C)C#N.CCCCCC>[Br:16][CH2:15][C:14]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[O:3][CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 23136282HCID 23136282, compound

Product 1

HCID 58306846HCID 58306846, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 8058HexaneSolvent

Procedure

To a mixture of ethyl 3-ethoxy-4-methylbenzoate (2.0 g), N-bromosuccinimide (1.9 g) and ethyl acetate (40 mL) was added 2,2′-azobis(2-methylpropionitrile) (15 mg), followed by stirring for 14 hours under heating with reflux. The mixture was left to be cooled, hexane was added thereto, the precipitated solid was separated by filtration, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane:5/95) to obtain ethyl 4-(bromomethyl)-3-ethoxybenzoate (2.4 g).

Workup

  1. temperatureunder heating
  2. temperaturewith reflux
  3. waitThe mixture was left
  4. temperatureto be cooled
  5. customthe precipitated solid was separated by filtration
  6. concentrationthe obtained filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane:5/95)

Sources & evidence

ORD record
ord-f9de10e459c14630af8718dfa6601824
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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