Dimethyl Disulfide → 1-(2-Chloro-1-methyl-1-methylsulfanyl-ethyl)-4-fluorobenzene

HRID 898838Notes

Reaction equation

S(Cl)([Cl:4])(=O)=O.CS[S:8][CH3:9].[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([CH3:17])=[CH2:16])=[CH:13][CH:12]=1>COCCOC>[Cl:4][CH2:16][C:15]([C:14]1[CH:18]=[CH:19][C:11]([F:10])=[CH:12][CH:13]=1)([CH3:17])[S:8][CH3:9]

Participants

Conditions

Temperature: -40 °C

Procedure

While cooling to −40° C., sulfuryl chloride (2.9 mL, 37 mmol) was added dropwise to a solution of dimethyl disulfide (3.3 mL, 37 mmol) in 1,2-dimethoxyethane (20 mL) under nitrogen atmosphere, and the mixture was stirred for 10 min. The obtained solution was added dropwise to a solution of 4-fluoro-α-methylstyrene (10 g, 73 mmol) in 1,2-dimethoxyethane (20 mL) while maintaining a temperature below −30° C. After stirring for 1 hour at room temperature, the solution was evaporated to give a crude product of the title compound. The obtained product was used in the next step without further purification.

Workup

temperaturewhile maintaining a temperature below −30° C
stirringAfter stirring for 1 hour at room temperature
customthe solution was evaporated

Sources & evidence

ORD record: ord-5ef2f7a6e521428a9955ff28d0290618
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351825B2

Reaction notes

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