3-Bromobiphenyl → 3-Phenylbenzene-1-sulfonyl chloride

Temperature

-78 °C

3-Bromobiphenyl (1.5 g, 6.4 mmol) was dissolved in ether (15 ml) and cooled to −78° C. t-Butyllithium (1.7 M solution in hexane, 3.8 ml, 6.4 mmol) was added dropwise under constant stirring and an argon atmosphere. The resultant reaction mixture was stirred at −10° C. to −5° C. for 6 h. The reaction mixture was cooled to −78° C. and sulfuryl chloride (0.64 ml, 6.4 mmol) was added dropwise. After completion of the 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 crude product, which was purified by column chromatography, using hexane followed by 5% ethyl acetate in hexane as eluent, to give 3-biphenylsulfonyl chloride as an oil (0.8 g, 49% yield).

1. additionwas added dropwise
2. customThe resultant reaction mixture
3. stirringwas stirred at −10° C. to −5° C. for 6 h
4. additionAfter completion of the addition
5. customto attain ambient temperature
6. stirringstirred for 1 h
7. washwashed with water
8. dry with materialthe organic layer dried over anhydrous MgSO4
9. customRemoval of the solvent under reduced pressure
10. customgave crude product, which
11. customwas purified by column chromatography

ORD record

ord-ec29df38969a48e38c05586bd13739d9

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613804B2