Novel facile method for the synthesis of methyl 2-fluoro-3-hydroxypropanoate from Claisen salts and formaldehyde in water

Abstract

Methyl 2-fluoro-3-hydroxypropanoate (MFHP) and its derivative methyl 3-chloro-2-fluoropropanoate (MCFP) are easily converted into methyl 2-fluoroacrylate (MFA). A roundabout strategy was put forward based on MFHP to overcome the shortcomings of MFA to extend its storage life and reduce its cost of shipment and storage. In our work, a novel and facile method for the synthesis of MFHP was developed based on Claisen salts and formaldehyde in water as followed: 37% formaldehyde aqueous (9.0 equiv.) was dropped into the aqueous of Claisen salt (1.0 equiv.) and NaHCO₃ (1.0 equiv.) at room temperature for 2-3 h to obtain MFHP in yield of 81.3%.

Graphical Abstract

Keywords:

• Methyl 2-fluoro-3-hydroxypropanoate
• Claisen salt
• water
• methyl 3-chloro-2-fluoropropanoate
• methyl 2-fluoroacrylate

Disclosure statement

The authors declare no conflict of interest.

Additional information

Funding

This work was supported by the National Natural Science Foundation of China (81502022 and 21702153) and Natural Science Foundation of Xiaogan, Hubei Province, China (XGKJ2019010046).