5-Benzyloxy-2-fluoro-4-methylaniline → 5-Benzyloxy-2-fluoro-4-methylphenol

HRID 393593

Reaction equation

N([O-])=[O:2].[Na+].[CH2:5]([O:12][C:13]1[C:14]([CH3:21])=[CH:15][C:16]([F:20])=[C:17]([CH:19]=1)N)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O.C(O)(=O)C.S(=O)(=O)(O)O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[Cu]=O>[CH2:5]([O:12][C:13]1[C:14]([CH3:21])=[CH:15][C:16]([F:20])=[C:17]([OH:2])[CH:19]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of sodium nitrite (1.68 g, 24 mmol) in water (3.5 ml) was added to a solution of 5-benzyloxy-2-fluoro-4-methylaniline (4.7 g, 20 mmol) in acetic acid (25 ml) and 70% sulphuric acid (25 ml) at 10° C. The mixture was stirred at 10° C. for 20 minutes and a solution of copper(II)nitrate trihydrate (481 g, 2 mol) in water (790 ml) followed by copper(II)oxide (3 g, 19 mmol) was added. The mixture was stirred for 3 hours then extracted with ethyl acetate. The organic layer was washed with water, brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with petroleum ether/ether (85/15) to give 5-benzyloxy-2-fluoro-4-methylphenol (1.25 g, 27%) as an orange oil.

Workup

additionwas added
stirringThe mixture was stirred for 3 hours
extractionthen extracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried (MgSO4)
customthe solvent removed by evaporation
customThe residue was purified by column chromatography
washeluting with petroleum ether/ether (85/15)

Sources & evidence

ORD record: ord-7113a17c42294fafb4f7216afb6af101
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809097B1

Linked notes

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