ChemicalBook CAS DataBase List (R)-(+)-2-BROMOPROPIONIC ACID

(R)-(+)-2-BROMOPROPIONIC ACID synthesis

8synthesis methods

Product Name:(R)-(+)-2-BROMOPROPIONIC ACID
CAS Number:10009-70-8
Molecular formula:C3H5BrO2
Molecular Weight:152.97

66423-08-3 Synthesis

(S)-2-((Methylsulfonyl)oxy)propanoic acid

66423-08-3
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10009-70-8
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Yield: 45%

Reaction Conditions:

Stage #1:(S)-2-(methylsulfonyloxy)propionic acid with lithium bromide in toluene at 60; for 1 h;
Stage #2: in water;toluene at 20; for 0.5 h;

Steps:

28 (Example 28) (R)-2-Bromopropionic acid
(Example 28) (R)-2-Bromopropionic acid lithium bromide (0.26 g) was added to a mixture prepared by adding 10 ml of toluene to 0.50 g of (S)-2-methanesulfonyloxypropionic acid (obtained in Example 16), the resulting mixture was stirred at 60°C for 1 hour and then cooled to 20°C, 5 ml of pure water was added and, after 30 minutes of stirring at 20°C, the organic layer was separated.. The thus-obtained organic layer contained 0.19 g of (R) -2-bromopropionic acid (yield 45%, optical purity 92.3% ee).. The rate of configuration inversion from methyl L-lactate was 92.3%.

References:

KANEKA CORPORATION EP1422215, 2004, A1 Location in patent:Page 23

338-69-2 Synthesis