Hydrochloric Acid → 4-Bromo-2-(4,5-dihydroisoxazol-3-yl)-3-methylbenzenesulfonyl chloride

HRID 1061102

Reaction equation

[Br:1][C:2]1[CH:8]=[CH:7][C:5](N)=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:3]=1[CH3:14].[ClH:15].N([O-])=O.[Na+].[S:20](=[O:22])=[O:21]>C(O)(=O)C.O.[Cu](Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([S:20]([Cl:15])(=[O:22])=[O:21])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:3]=1[CH3:14]

Participants

Conditions

Temperature: 5 °C

Procedure

At 15° C., a solution of 9 g (35 mmol) of 4-bromo-2-(4,5-dihydro-isoxazol-3-yl)-3-methylaniline in 50 ml of glacial acetic acid is added to 15 ml of conc. hydrochloric acid. At 5-10° C., a solution of 2.44 g (35 mmol) of sodium nitrite in 10 ml of water is then added dropwise, and the mixture is stirred at 5° C. for 1 hour. This solution is then added dropwise at room temperature to a mixture of a solution of 47 g (0.74 mol) of sulfur dioxide in 100 ml of glacial acetic acid and a solution of 2.23 g (13 mmol) of copper(II) chloride in 5 ml of water. The mixture is stirred at room temperature for 1 hour and then poured onto 300 ml of ice-water and extracted with methylene chloride. The organic phase is washed with water, dried with magnesium sulfate and concentrated.

Workup

stirringThe mixture is stirred at room temperature for 1 hour
extractionextracted with methylene chloride
washThe organic phase is washed with water
dry with materialdried with magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-635e194922504ea1aa02a15414934e3c
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525204B1

Linked notes

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