Water → Methyl 5-bromo-3-chloro-4-methoxy-2-(methoxymethoxy)benzoate
Reaction equation
[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([Cl:13])[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH3:18][O:19][CH2:20]Cl.O>C1COCC1>[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([Cl:13])[C:5]([O:12][CH2:18][O:19][CH3:20])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 5-bromo-3-chloro-2-hydroxy-4-methoxybenzoate (5.00 g) in THF (120 mL) was added sodium hydride (1.01 g) under ice-cooling, and the mixture was stirred for 1 hr under nitrogen atmosphere. To this reaction mixture was added dropwise chloromethyl methyl ether (1.63 g), and the mixture was stirred at 20° C. for 16 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (3.08 g).
Workup
- temperaturecooling
- stirringthe mixture was stirred at 20° C. for 16 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether)
Sources & evidence
- ORD record
- ord-5bc0d4ac9bf04783b8db2187b9c9219c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315458B2
Reaction notes
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