Water → Ethyl 2-(2-acetyl-4-bromophenoxy)acetate
Reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][C:9]([C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:12]=1[OH:18])=[O:10].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:18][C:12]1[CH:13]=[CH:14][C:15]([Br:17])=[CH:16][C:11]=1[C:9](=[O:10])[CH3:8])[CH3:7]Participants
Procedure
Ethyl bromoacetate (0.619 mL) was added to a mixture of 5-bromo-2-hydroxyacetophenone (1.0 g) and potassium carbonate (0.964 g) in N,N-dimethylformamide (10 mL), and the mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford ethyl(2-acetyl-4-bromophenoxy)acetate as a crude product. The crude ethyl(2-acetyl-4-bromophenoxy)-acetate was dissolved in ethanol (5 mL). A 2 mol/L aqueous solution of sodium hydroxide (5 mL) was added to the solution, and the mixture was stirred for 1 hr. The reaction mixture was made acidic with an addition of 2 mol/L hydrochloric acid (7 mL), and then ethyl acetate and brine were added. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate and n-hexane to afford the title compound (0.851 g).
Workup
- customThe organic layer was separated
- washwashed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-6a4b6110b3964b28a26ac2fbf8415a0d
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07417169B2
Reaction notes
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