3-(2-CHLORO-PHENYLSULFANYL)-PROPIONIC ACID synthesis

6synthesis methods

Product Name:3-(2-CHLORO-PHENYLSULFANYL)-PROPIONIC ACID
CAS Number:99585-16-7
Molecular formula:C9H9ClO2S
Molecular Weight:0

6320-03-2 Synthesis

6320-03-2
147 suppliers
$12.00/1g

539-74-2 Synthesis

539-74-2
277 suppliers
$5.00/5g

3-(2-CHLORO-PHENYLSULFANYL)-PROPIONIC ACID

99585-16-7
12 suppliers
$65.00/50mg

Yield:99585-16-7 93%

Reaction Conditions:

Stage #1: 2-chlorothiphenol;Ethyl 3-bromopropionatewith potassium hydroxide;ethanol;water at 20; for 64 h;
Stage #2: with hydrogenchloride;water pH=1;

Steps:

44

Example 44 - Preparation of 3-(2-Chloro-phenylsulfanyl)-propionic acid (Compound 44); [137] To a 500 mL round bottom flask, equipped with a magnetic stir bar, was added 2- chlorobenzenethiol (2.00 mL, 18 mmol), ethyl 3-bromopropionate (2.26 mL, 18 mmol), potassium hydroxide (2.08 g, 37 mmol), and 50 mL ethyl alcohol. The reaction mixture was stirred at room temperature for 4 hours, 15 mL water was added and the mixture was stirred for 42 hours at room temperature. Ethyl 3-bromopropionate (1.70 mL, 13 mmol) and potassium hydroxide (2.19 g, 39 mmol) were added in three aliquots during the next 18 hours. Solvent was removed under reduced pressure. Residual was dissolved in 150 mL water and acidified with aqueous 1 N hydrochloric acid solution to pH 1. Filtration yielded the product (3.56 g, 93%) as a white solid. IH NMR (d6-DMSO): δ 12.41, s, IH (COOH); δ 7.46, dd, IH (aryl H); δ 7.40, dd, IH (aryl H); δ 7.34, dt, IH (aryl H); δ 7.20, dt, IH (aryl H); 5 3.18, t, 2H (CH₂ α to S); δ 2.59, t, 2H (CH₂ α to COOH).

References:

WO2008/14430,2008,A1 Location in patent:Page/Page column 52