Methyl iodide → Methyl 2-(3-bromo-2-methoxyphenyl)acetate
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[C:6]=1[OH:12].[C:14](=O)([O-])[O-].[K+].[K+].IC>CC#N.CCOC(C)=O.O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[C:6]=1[O:12][CH3:14]Participants
7
Conditions
- Temperature
- 50 °C
Procedure
To a solution of (3-bromo-2-hydroxy-phenyl)-acetic acid methyl ester (866 mg, 3.5 mmol, 1 eq.) and potassium carbonate (2.44 g, 17.7 mmol, 5 eq.) in MeCN (9 mL), iodomethane (0.67 mL, 10.6 mmol, 3 eq.) was added. The resulting mixture was stirred at 50° C. for 2 hours. The reaction mixture was diluted with AcOEt and water. The layers were separated and the aq. phase was extracted with AcOEt (2×). The comb. org. layers were dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as an orange oil. The product was used without further purification.
Workup
- customThe layers were separated
- extractionthe aq. phase was extracted with AcOEt (2×)
- dry with materiallayers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-059b8d3803e1430a89e83f9f1a70f243
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255090B2
Reaction notes
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