Nitric Acid → Methyl 5-nitro-2-(trifluoromethoxy)benzoate
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:19])([F:18])[O:7][C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]>>[CH3:13][O:12][C:10](=[O:11])[C:9]1[CH:14]=[C:15]([N+:1]([O-:4])=[O:2])[CH:16]=[CH:17][C:8]=1[O:7][C:6]([F:5])([F:19])[F:18]Participants
Conditions
- Temperature
- 60 °C
Procedure
In a three-necked round bottom flask, equipped with a thermometer and a separatory funnel, HNO3 (5 mL fuming, 100%) was cooled in an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added to the cooled HNO3 within 0.5 hour while keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was added to ice water and an oil separated. The oily residue was added water (50 mL), neutralised with an aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester.
Workup
- temperaturewas cooled in an ice bath
- customthe temperature below 15° C
- customan oil separated
- additionThe oily residue was added water (50 mL)
- extractionextracted with ethyl acetate (25 mL)
- extractionThe aqueous phase was extracted with ethyl acetate (15 mL) once more
- washThe combined organic phases were washed with saturated sodium chloride (2×15 mL)
- dry with materialdried (magnesium sulphate)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-46f5835c70dc4103ae11c3a0124e4789
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562807B2
Reaction notes
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