Reaktion #465612

Reaktionsgleichung

2-Bromobiphenyl

n-Butyllithium

sulfuryl chloride

→

2-bi-phenylsulfonyl chloride

Ausbeute 51.4%

Lösungsmittel

ether

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   SonstigeThe resultant reaction mixture
3. 3
   workup.STIRRINGwas stirred at -70° C. to -60° C. for 1 h
4. 4
   workup.ADDITIONAfter addition
5. 5
   Sonstigeto attain ambient temperature
6. 6
   workup.STIRRINGstirred for 1 h
7. 7
   Waschenwashed with water
8. 8
   Trocknenthe organic layer dried over anhydrous MgSO4
9. 9
   SonstigeRemoval of the solvent under reduced pressure
10. 10
    Sonstigegave a crude product, which
11. 11
    Sonstigewas purified by column chromatography

Vorschrift

2-Bromobiphenyl (2.33 g, 10 mmol) was dissolved in ether (10 ml) and cooled to -78° C. n-Butyllithium (2.5 M solution in hexane, 4.8 ml, 12 mmol) was added dropwise under constant stirring and an argon atmosphere. The resultant reaction mixture was stirred at -70° C. to -60° C. for 1 h. The reaction mixture was cooled to -78° C. and sulfuryl chloride (0.88 ml, 11 mmol) was added dropwise. After addition, the reaction mixture was allowed to attain ambient temperature slowly and stirred for 1 h. The reaction mixture was diluted with ethyl acetate (50 ml), washed with water and the organic layer dried over anhydrous MgSO4. Removal of the solvent under reduced pressure gave a crude product, which was purified by column chromatography, using hexane followed by 5% ethyl acetate in hexane as eluent, to give 2-bi-phenylsulfonyl chloride as a solid (1.3 g, 51% yield).

Quelle