Tetrahydrofuran → Benzene, 1-methyl-3-(methylthio)-

Add 1M 3-methyl-phenylmagnesium bromide in THF (25 mL, 25 mmol) to −30° C. diethyl ether (50 mL). Add dimethyl disulfide (1.8 mL, 20 mmol) to the reaction over 3 minutes allowing the reaction to warm to room temperature. Dilute the reaction in H2O (75 mL) and diethyl ether (50 mL). Separate and extract the cloudy aqueous layer with diethyl ether (25 mL). Combine the organic layers and wash with H2O (25 mL). Dry the organic layer with Na2SO4 (30 g), filter over Celite 501 (10 g) and concentrate in vacuo to give 3.0 g of crude material. Combine with another batch of crude title compound that yielded 6.0 g crude. Chromatograph the entire 9.0 g crude on a SiO2 column in hexanes to give 7.2 g (70%) of 1-methyl-3-methylsulfanyl-benzene.

1. customthe reaction
2. additionDilute
3. customSeparate
4. extractionextract the cloudy aqueous layer with diethyl ether (25 mL)
5. washCombine the organic layers and wash with H2O (25 mL)
6. dry with materialDry the organic layer with Na2SO4 (30 g)
7. filtrationfilter over Celite 501 (10 g)
8. concentrationconcentrate in vacuo
9. customto give 3.0 g of crude material
10. customCombine with another batch of crude title compound that yielded 6.0 g crude

ORD record

ord-65b3c7f9c8cb4a4e9e784b53da2010b9

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585977B2