Ethyl Acetate → HCID 59342581, compound

HRID 1908893Notes

Reaction equation

HRID 1908893 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-c7ad16d6f8fd4822b3378c284a8eb9c1
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

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