Dimethyl Sulfone → 2-(3-Iodophenyl)ethyl methyl sulfone

Temperature

-78 °C

To a solution of dimethyl sulfone (1 eq.) in 60 mL of anhydrous THF (0.2 M) was added, at −78° C., n-butyl lithium (1.6 M hexane solution, 1.2 eq.) over a period of 10 min. The resulting mixture was stirred at −78° C. for 1 h. To the now yellow solution was added, at −78° C., 3-iodobenzyl bromide (I eq.). The reaction mixture was then slowly warmed to RT over 16 h. The reaction was carefully quenched with 10% aq. HCl and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a viscous oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) followed by trituration with hexanes afforded the title compound as a white crystalline solid.

1. additionTo the now yellow solution was added, at −78° C.
2. temperatureThe reaction mixture was then slowly warmed to RT over 16 h
3. customThe reaction was carefully quenched with 10% aq. HCl
4. extractionextracted with ether
5. washThe combined organic extracts were washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customConcentration of the filtrate in vacuo afforded a viscous oil
9. customPurification of the crude product
10. customthus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

ORD record

ord-2919ee22e19842ef9a5b17369d850419

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2