Ammonium Chloride → 1,2-Bis(2-chloro-5-methoxyphenyl)disulfane

To a solution of 2-bromo-1-chloro-4-methoxybenzene (4.42 g, 19.9 mmol) in THF stirring at −10° C. under nitrogen was added isopropylmagnesium chloride (9.9 mL, 19.9 mmol, 2M in THF). The reaction was allowed to warm to ambient temperature stirred for 4 hours. The reaction was cooled to −40° C. and zinc(II) chloride (19.9 mL, 19.9 mmol, 1M in ether) was added and the solution stirred for 30 minutes. The reaction was cooled to −78° C. and sulfurothioyl dichloride (0.80 mL, 9.9 mmol) was added. After stirring for 15 minutes at −78° C., saturated NH4Cl was added and the mixture was warmed to ambient temperature and extracted multiple times with EtOAc. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to give a residue which was purified by silica chromatography (10% EtOAc in hexanes) to afford the title compound (1.52 g, 21.9% yield).

1. temperatureThe reaction was cooled to −40° C.
2. stirringthe solution stirred for 30 minutes
3. temperatureThe reaction was cooled to −78° C.
4. stirringAfter stirring for 15 minutes at −78° C.
5. temperaturethe mixture was warmed to ambient temperature
6. extractionextracted multiple times with EtOAc
7. dry with materialThe combined organic layers were dried with sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a residue which
11. customwas purified by silica chromatography (10% EtOAc in hexanes)

ORD-Eintrag

ord-19e0f2b0f7874b5598fc5f4e4ad9e4fb

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08022223B2