Potassium Acetate → 2,6-Dibromobenzyl acetate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH2:9]Br.[C:11]([O-:14])(=[O:13])[CH3:12].[K+]>CN(C)C=O>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[CH2:9][O:14][C:11](=[O:13])[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To 1,3-Dibromo-2-bromomethyl-benzene (3.35 g, 10.2 mmol) was added potassium acetate (4.00 g, 40.8 mmol) and 25 mL N,N-dimethylformamide. This was heated at 70° C. for 20 minutes. The resulting mixture was partitioned between water and ethyl acetate. The ethyl acetate layer was washed with water, washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 0 to 5% ethyl acetate hexanes) to yield Acetic acid 2,6-dibromo-benzyl ester (1.92 g, 6.23 mmol). 1HNMR (300 MHz, CDCl3) δ 2.12 (s, 3H), 5.42 (s, 2H), 7.08 (t, J=8 Hz, 1H), and 7.58 (d, J=8 Hz, 2H).
Workup
- customThe resulting mixture was partitioned between water and ethyl acetate
- washThe ethyl acetate layer was washed with water
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- custompurified by flash chromatography (gradient elution 0 to 5% ethyl acetate hexanes)
Sources & evidence
- ORD record
- ord-84ca19136d914a5ea195115e51242ff5
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683064B2
Reaction notes
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