Réaction #6786

Équation de réaction

4-methylbenzenethiol

NaH

Ethylbromoacetate

→

colorless oil

Rendement 99.0%

p-Tolylsulfanyl-acetic acid ethyl ester

Rendement 99.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGfurther stirred at room temperature for 3 h
2. 2
   AutreThe solvent was removed under vacuum
3. 3
   workup.DISSOLUTIONThe residue was dissolved in oil
4. 4
   ExtractionHCl and extracted by ethylacetate
5. 5
   LavageThe combined organic phase was washed successively with saturated NaHCO3 solution, water and brine
6. 6
   Séchagethen dried over Na2SO4
7. 7
   AutreEvaporation of organic phase

Mode opératoire

A solution of 4-methylbenzenethiol (5 g, 40.25) in dry THF was added dropwise to a suspension of NaH (60% in mineral oil, 1.98 g, 48.30) in THF at room temperature and stirred for 30 min. under N2 atmosphere. Ethylbromoacetate (4.9 mL, 44.27) was added slowly to this solution and further stirred at room temperature for 3 h. The solvent was removed under vacuum. The residue was dissolved in oil. HCl and extracted by ethylacetate. The combined organic phase was washed successively with saturated NaHCO3 solution, water and brine then dried over Na2SO4. Evaporation of organic phase yielded 8.46 g (99%) colorless oil. 1H NMR (CDCl3): δ 1.22 (t, J=7.2 Hz, 3H), 2.32 (s, 3H), 3.57 (s, 2H), 4.14 (q, J=7.2 Hz, 2H), 7.11 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H). EIMS m/z 210 (M+1), 233 (M+23).

Source