Ethyl Bromide → Ethyl 4-ethoxy-3-hydroxybenzoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([OH:12])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH3:21]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:20][CH3:21])=[C:7]([OH:12])[CH:6]=1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5 g (27.2 mmol) of 3,4-Dihydroxy-benzoic acid ethyl ester was dissolved in 100 ml DMF and 3.75 g (27.2 mmol) of potassium carbonate was added. The solution was cooled to 0° C. and a solution of 2.96 g (27.2 mmol) ethyl bromide in 10 ml DMF was added dropwise. The solution was stirred for 16 h at room temperature (RT). The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/4).
Workup
- customThe solvent was removed under reduced pressure
- washthe solution was washed three times with water
- dry with materialThe organic phase was dried with magnesium sulphate
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customThe residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/4)
Sources & evidence
- ORD record
- ord-ce3c0dac085d448497c5da2aacc7af88
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067665B2
Reaction notes
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