Sulfuryl chloride → Ethyl 2-chloro-2-(methylsulfanyl)acetate

HRID 2091464Notes

Reaction equation

HRID 2091464 reaction equation
[CH3:1][S:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:12])(=O)=O>ClCCl>[CH2:7]([O:6][C:4](=[O:5])[CH:3]([Cl:12])[S:2][CH3:1])[CH3:8]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 78199Ethyl (methylthio)acetate

Product 1

HCID 10877535Ethyl 2-chloro-2-(methylsulfanyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a Stirred Solution of ethyl (methylthio)acetate (10.8 ml) in dichloromethane (300 ml) cooled to −15° C. is added dropwise sulphuryl chloride (8.1 ml). The mixture is allowed to warm to room temperature over two hours and then concentrated under reduced pressure to give crude chloro-methylsulfanyl-acetic acid ethyl ester as a colourless liquid. The product is used in the next step without further purification. 1H NMR (CDCl3) δ ppm: 5.35 (1H, s); 4.25 (2H, m); 2.30 (3H, s); 1.30 (3H, t).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-18456d3d365b443db2b2d23227f97c2e
Source dataset
uspto-grants-2013_05
Patent number
US08440595B2

Reaction notes

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