Reaktion #73877

Reaktionsgleichung

NaH

1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid

SOCl2

MeSO2NH2

→

title compound

Ausbeute 86.1%

N-[1-(4-Bromo-phenyl)-cyclopropanecarbonyl]-methanesulfonamide

Ausbeute 86.1%

Lösungsmittel

CH2Cl2

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethen evaporated
2. 2
   Sonstigeto afford a dark oil
3. 3
   Extraktionextracted with CH2Cl2
4. 4
   Waschenwashed with water (2×)
5. 5
   Sonstigeevaporated to ˜100 mL
6. 6
   workup.ADDITIONHexane (300 mL) was added
7. 7
   Filtrationthe product collected by filtration

Vorschrift

1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid (22 g, 91.3 mmol) and SOCl2 (13.6 mL, 183 mmol) in CH2Cl2 were heated together for 1.5 hours then evaporated to afford a dark oil. This oil was added via syringe over 30 minutes to a mixture of MeSO2NH2 (19 g, 200 mmol) in THF (250 mL) that was pre-treated at room temperature with NaH (60% in oil; 8.0 g, 200 mmol) for 1.5 hours. After a further 20 minutes, the mixture was poured into water, acidified and extracted with CH2Cl2, washed with water (2×) and evaporated to ˜100 mL. Hexane (300 mL) was added and the product collected by filtration to yield the title compound (25 g).

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