Methyl iodide → 2-[(Methylsulfanyl)methyl]-1,1'-biphenyl

Temperature

60 °C

A mixture of biphenyl-2-yl-methanethiol (4 g, 20 mmol) in methanol (27 mL) and sodium methoxide in methanol (0.5 M, 40 mL) was heated at 60° C. for 0.5 h, cooled, treated with methyl iodide (3.7 mL, 60 mmol) and re-heated at 60° C. for 0.5 h. After cooling to room temperature, the reaction mixture was quenched with ice-water, acidified (pH˜2) and extracted with ethyl acetate (3×50 mL). Combined organic layer was washed with water (1×50 mL) and brine (1×50 mL), dried (MgSO4), and concentrated to give a crude product that was passed through a bed of silica (solvent: ethyl acetate) to give 3.3 g of 2-methylsulfanylmethyl-biphenyl (yellow oil) that was directly used in the next step.

1. temperaturecooled
2. temperaturere-heated at 60° C. for 0.5 h
3. temperatureAfter cooling to room temperature
4. customthe reaction mixture was quenched with ice-water
5. extractionextracted with ethyl acetate (3×50 mL)
6. washCombined organic layer was washed with water (1×50 mL) and brine (1×50 mL)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customto give a crude product that

ORD record

ord-e3aa70915ad8463ebf2b18ee2138c9e0

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07981907B2