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

HRID 393614

Reaction equation

N([O-])=[O:2].[Na+].[C:5](=[O:18])([O:16][CH3:17])[O:6][C:7]1[CH:12]=[C:11](N)[C:10]([F:14])=[CH:9][C:8]=1[CH3:15]>O.S(=O)(=O)(O)O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[Cu]=O>[C:5](=[O:18])([O:16][CH3:17])[O:6][C:7]1[CH:12]=[C:11]([OH:2])[C:10]([F:14])=[CH:9][C:8]=1[CH3:15]

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 dropwise to a solution of (5-amino-4-fluoro-2-methylphenyl) methyl carbonate (3.93 g, 20 mmol) in 35% sulphuric acid (48 ml) at 0° C. The 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) was 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 (4-fluoro-5-hydroxy-2-methylphenyl) methyl carbonate (2.13 g, 53%) as a yellow solid.

Workup

additionwas 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-35fce86474504acf894dc7bb42ac50b5
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809097B1

Linked notes

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