Boron trifluoride etherate → 2-(Ethyldisulfanyl)-6-methylphenol

Diethyl disulfide (14.24 ml, 116 mmol) and BF3.OEt2 (14.66 mml, 16.42 mmol) were added to a solution of 6,6′-disulfanediylbis(2-methylphenol) (Compound 104) (1.61 g, 5.78 mmol) in dichloromethane (30 ml), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was then quenched by slowly adding a saturated NaHCO3 solution dropwise thereto at 0° C., after which the mixture was extracted with ethyl acetate and the organic layer was washed with water. The organic extract was then dried over sodium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→90/10) to afford 2-(ethyldisulfanyl)-6-methylphenol (Compound 105) (1.67 g, 72%).

1. customThe reaction mixture was then quenched
2. additionby slowly adding a saturated NaHCO3 solution dropwise
3. extractionat 0° C., after which the mixture was extracted with ethyl acetate
4. washthe organic layer was washed with water
5. extractionThe organic extract
6. dry with materialwas then dried over sodium sulfate
7. concentrationconcentrated
8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→90/10)

ORD record

ord-4b5a49211a85436685818287c86c66ef

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409952B2