Water → Methyl 3-methyl-5-nitro-2-trifluoromethylsulfonyloxybenzoate

Methyl 2-hydroxy-3-methyl-5-nitrobenzoate (Reference Compound No. 1-4-(2), 6.0 g, 28.4 mmol) was dissolved in tetrahydrofuran (200 mL), then triethylamine (16.7 mL, 120 mmol) and trifluorometanesulfonyl chloride (6.23 mL, 58.5 mmol) were added thereto, and then the reaction mixture was stirred at room temperature overnight. Water (500 mL) was added to the reaction mixture, then the whole was extracted with ethyl acetate (500 mL). The organic layer was washed with 0.2N aqueous NaOH solution (200 mL, twice) and saturated brine (200 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (9.32 g) as a pale yellow oil. (Yield 96%)

1. extractionthe whole was extracted with ethyl acetate (500 mL)
2. washThe organic layer was washed with 0.2N aqueous NaOH solution (200 mL
3. dry with materialtwice) and saturated brine (200 mL) successively, dried over anhydrous magnesium sulfate
4. customthe solvent was removed under reduced pressure
5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

ORD record

ord-8a26bedd2dce48e8b635e871ae5cd636

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420635B2