5-Amino-4-fluoro-2-methylphenyl Methoxyformate → (4-Fluoro-5-hydroxy-2-methylphenyl) methyl carbonate
Reaction equation
N([O-])=[O:2].[Na+].[F:5][C:6]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][C:7]=1N>O.S(=O)(=O)(O)O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[Cu]=O>[F:5][C:6]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][C:7]=1[OH:2]Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 0 °C
Procedure
A solution of sodium nitrite (1.63 g, 23 mmol) in water (19ml) and ice (48 g) was added dropwsie to a solution of 2-fluoro-5-methoxycarbonyloxy-4-methylaniline (3.93 g, 20 mmol) in 35% sulphuric acid (48 ml) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes and a solution of copper(II)nitrate trihydrate (467 g, 1.93mol) in water (780 ml). followed by copper(II)oxide (2.65 g, 18 mmol) were added. The solution was extracted with ethyl acetate, the organic layer was washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with petroleum ether/ethyl acetate (8/2) to give 2-fluoro-5-methoxycarbonyloxy-4-methylphenol (2.13 g, 53%) as a yellow solid.
Workup
- additionwere added
- extractionThe solution was extracted with ethyl acetate
- washthe organic layer was washed with brine
- dry with materialdried (MgSO4)
- customthe solvent removed by evaporation
- customThe residue was purified by column chromatography
- washeluting with petroleum ether/ethyl acetate (8/2)
Sources & evidence
- ORD record
- ord-ad5af74c9eca43bc8b4e268ab88d4624
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05962458
Reaction notes
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