Ethyl Acetate → HCID 59342581, compound

HRID 15650Notes

Reaction equation

HRID 15650 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[C:7]([CH2:13]Br)[CH:6]=1)(=[O:3])[CH3:2].[C:15]([O-:18])(=[O:17])[CH3:16].[Na+].C(OCC)(=O)C>CN(C)C=O>[C:15]([O:18][CH2:13][C:7]1[CH:6]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:10]=[C:9]([CH3:11])[C:8]=1[Br:12])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 151846864-Bromo-3-(bromomethyl)-5-methylphenyl acetate

Product 1

HCID 59342581HCID 59342581, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromo-3-(bromomethyl)-5-methylphenyl acetate (11.7 g, 36.3 mmol) in N,N-dimethylformamide (60 mL) was added sodium acetate (5.96 g, 72.6 mmol), and the mixture was stirred at 70° C. for 4 hr under nitrogen atmosphere. Ethyl acetate was added to the reaction mixture, and the mixture was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75) to give the title compound (7.29 g, yield 67%) as a pale-yellow oil.

Workup

  1. washthe mixture was washed successively with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75)

Sources & evidence

ORD record
ord-3eecbf4e09704a798a917dd7e05d50e0
Source dataset
uspto-grants-2010_06
Patent number
US07732626B2

Reaction notes

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