Réaction #476530

Équation de réaction

triethylamine

benzenethiol

1-chloroethyl chloroformate

→

product

Rendement 98.5%

O-(1-Chloroethyl) S-Phenyl Thiocarbonate

Rendement 98.5%

Solvants

dichloromethane

CH2Cl2

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was removed from the ice bath
2. 2
   LavageThe reaction was washed with water (3×500 mL)
3. 3
   Autrethe organic phase was separated
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated in vacuo

Mode opératoire

A solution of benzenethiol (50 g, 450 mmol) and 1-chloroethyl chloroformate (65 g, 450 mmol) in CH2Cl2 (300 mL) was cooled to 0-4° C. in an ice-water bath. To the mixture was added a solution of triethylamine (450 mmol) in dichloromethane (200 mL) dropwise over 30 min. The reaction was removed from the ice bath and stirred at ambient temperature for 12 h. The reaction was washed with water (3×500 mL), the organic phase was separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the product as a pale yellow liquid (96 g, 98.5%). 1H NMR (CDCl3, 400 MHz): δ 1.82 (d, 3H), 6.6 (q, 1H), 7.2-7.4 (m, 5H).

Source