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ChemicalBook CAS DataBase List 4-METHOXY-2-METHYL-1-METHYLSULFANYL-BENZENE
22583-04-6

4-METHOXY-2-METHYL-1-METHYLSULFANYL-BENZENE synthesis

3synthesis methods
27060-75-9 Synthesis
2-Bromo-5-methoxytoluene

27060-75-9
277 suppliers
$8.00/5g

4-METHOXY-2-METHYL-1-METHYLSULFANYL-BENZENE

22583-04-6
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Yield:-

Reaction Conditions:

Stage #1: 4-bromo-3-methylanisolewith n-butyllithium in tetrahydrofuran;hexane at -78; for 1 h;
Stage #2: Dimethyldisulphide in tetrahydrofuran;hexane at 20; for 2 h;
Stage #3: with water;ammonium chloride in tetrahydrofuran;hexane;

Steps:

15.1.1

Step 1 : To the cold (-780C) solution of 2-bromo-5-methoxy toluene (8g, 0.04mol) in dryTHF (8OmL) under inert atmosphere, butyl lithium solution (1.6M solution in hexane; 36.8mL, 0.058mol) was added dropwise and the mixture was stirred for 1h at same temperature. Dimethyl disulphide (7.7mL, O.Oδmol) was then added dropwise and the reaction mixture was allowed to warm to room temperature over a period of 2h. The reaction mixture was quenched with sat. ammonium chloride solution and extracted in diethyl ether. The combined organic extracts were washed with water and brine and dried. The solvent was evaporated in vacuo to yield 6.5g of 2-methyl-4-methoxy thioanisole, which was used as such in Step 2 MS m/z 168 (M+).

References:

WO2009/30467,2009,A2 Location in patent:Page/Page column 107-108