Reaktion #484330

Reaktionsgleichung

4-bromo-2-(4,5-dihydro-isoxazol-3-yl)-3-methylaniline

hydrochloric acid

sulfur dioxide

sodium nitrite

→

4-bromo-2-(4,5-dihydroisoxazol-3-yl)-3-methyl-benzenesulfonyl chloride

Lösungsmittel

acetic acid

acetic acid

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture is stirred at room temperature for 1 hour
2. 2
   Extraktionextracted with methylene chloride
3. 3
   WaschenThe organic phase is washed with water
4. 4
   Trocknendried with magnesium sulfate
5. 5
   Einengenconcentrated

Vorschrift

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.

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