Methyl chloroformate → Methyl 3-chloro-2-[(methoxycarbonyl)oxy]-4-(trifluoromethyl)benzoate
Reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:12][CH2:13][O:14][CH3:15].C([Li])CCC.Cl[C:22]([O:24][CH3:25])=[O:23].C(=O)(O)[O-:27].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]([O:12][C:13]([O:14][CH3:15])=[O:27])=[C:4]([CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9])[C:22]([O:24][CH3:25])=[O:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-chloro-1-(methoxymethoxy)-3-(trifluoromethyl)benzene (11.8 g) in THF (100 mL) was added dropwise n-butyllithium (2.5M hexane solution) (21.0 mL) at −10° C., and the mixture was stirred for 2 hr. Then, to the reaction mixture was added dropwise a solution of methyl chloroformate (23.0 g) in THF (50.0 mL), and the mixture was stirred at 10° C. for 16 hr. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate (×2). The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (6.00 g).
Workup
- stirringthe mixture was stirred at 10° C. for 16 hr
- extractionthe mixture was extracted with ethyl acetate (×2)
- dry with materialThe organic layer was dried 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-f4cc3efe25134c95aec59f541b58eddd
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315458B2
Reaction notes
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