Water → Ethyl 3-bromofuran-2-carboxylate
Reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=[O:8].I[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([O:9][CH2:11][CH3:12])=[O:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A suspension of 3-bromofuran-2-carboxylic acid (23.5 g), iodoethane (11.8 mL) and potassium carbonate (25.6 g) in DMF (200 mL) was stirred at 60° C. overnight. The reaction mixture was poured into water, and the mixture was extracted with diethylether. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in hexane, passed through a silica gel (NH) layer, and the eluate was concentrated under reduced pressure to give the title compound (23.0 g).
Workup
- extractionthe mixture was extracted with diethylether
- washThe extract was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in hexane
- concentrationthe eluate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-99b39b7174094af394b8b10f1dc20bb3
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150588B2
Reaction notes
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