3-[(4-FLUOROPHENYL)THIO]PROPANOIC ACID synthesis
- Product Name:3-[(4-FLUOROPHENYL)THIO]PROPANOIC ACID
- CAS Number:19543-85-2
- Molecular formula:C9H9FO2S
- Molecular Weight:200.23
Yield:19543-85-2 94%
Reaction Conditions:
Stage #1: 4-Fluorothiophenolwith potassium hydroxide in ethanol;water at 60;
Stage #2: chloropropionic acidwith potassium carbonate in ethanol;water at 20 - 96; for 5.5 h;
Steps:
Synthesis of 4-chloro-6-fluoro-2H-thiochromene-3-carbaldehyde (7a)
A mixture (I) of 4-fluorothiophenol (10.75 g, 84mmol), potassium hydroxide (5.7 g, 87 mmol), ethanol (48 ml) and water (48 ml) were heated at 60°C. To a solution of 30% potassium carbonate solution (60 ml) was added β-chloropropionic acid (9.07 g, 84 mmol). The mixture (II) was stirred at room temperature for 0.5 h. The mixture of (I) and (II) was reflux at 96°C for 5 h. Then the mixture was cooled to room temperature and then the solution was added HCl to pH 2. The white solid was filtrated and the filter cake washed with water. After drying, compounds 5a (15.8 g, 94.0%) was obtained.
References:
Wang, Dan-Jiao;Hou, Zhuang;Xu, Hang;An, Ran;Su, Xin;Guo, Chun [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 22,p. 3574 - 3578] Location in patent:supporting information
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