Reaktion #64576

Reaktionsgleichung

3-fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl

3-Fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl

bromine

→

title compound

Ausbeute 81.8%

[3-Fluoro-2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl Bromide

Ausbeute 81.8%

Lösungsmittel

CCl4

CCl4

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise over 1.5 hour
2. 2
   Temperaturat reflux overnight
3. 3
   Temperaturthe solution was cooled
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was crystallized from EtOAc-hexane

Vorschrift

A solution of 1.08 g (3.36 mmol) of 3-fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl (from Step A) in 20 mL of CCl4 was stirred at reflux under irradiation from a 100-watt tungsten lamp as a solution of 3.5 mmol of bromine in approximately 13 mL of CCl4 was added dropwise over 1.5 hour. After being stirred at reflux overnight, the solution was cooled and concentrated. The residue was crystallized from EtOAc-hexane to give 1.10 g of the title compound as an off-white solid, mp 138°-140° C. (estimated purity 87%; contained minor unbrominated and dibrominated contaminants by TLC); mass spectrum (FAB) m/e 400, 402 (M+1)+.

Quelle