5-Amino-4-fluoro-2-methylphenyl Methoxyformate → (4-Fluoro-5-hydroxy-2-methylphenyl) methyl carbonate

HRID 279538

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

Conditions

Temperature: 0 °C

Procedure

A solution of sodium nitrite (1.63 g, 23 mmol) in water (19 ml) 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, 1.93 mol) 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-e70dd8e5684847159b21a5e6e481d2f3
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362336B1

Linked notes

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