Hydroxyamine hydrochloride → 1-(4-Bromophenyl)-2-(3-fluoro-4-methylthiophenyl)ethanone oxime

HRID 1597572Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[C:12]([F:18])[CH:11]=2)=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].C([O-])(=O)C.[Na+]>C(O)C.O.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:21][OH:22])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[C:12]([F:18])[CH:11]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 1-(4-bromophenyl)-2-(3-fluoro-4-methylthiophenyl)ethanone (1.50 g, 4.42 mmol) in a mixture of ethanol (12 ml) and water (6 ml) were added hydroxylamine hydrochloride (615 mg, 8.84 mmol) and anhydrous sodium acetate (715 mg, 8.84 mmol) at room temperature. The mixture was heated for 2 h at 75° C. and then diluted with diethyl ether (200 ml), washed with water (50 ml×2) and saturated sodium bicarbonate (50 ml×2), and dried over magnesium sulfate. Removal of solvent gave 1.56 g (˜100%) of 1-(4-bromophenyl)-2-(3-fluoro-4-methylthiophenyl)ethanone oxime as an orange solid.

Workup

washwashed with water (50 ml×2) and saturated sodium bicarbonate (50 ml×2)
dry with materialdried over magnesium sulfate
customRemoval of solvent

Sources & evidence

ORD record: ord-680ac932263c47f6a7681233ceb2ad87
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06294558B1

Reaction notes

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