US 12,441,677 B2
One step synthesis for alkyl 2-fluoroacrylates
Qingwu Jin, Bothell, WA (US); and Michael Whitacre, San Carlos, CA (US)
Assigned to VIFOR (INTERNATIONAL) LTD., St. Gallen (CH)
Appl. No. 17/755,981
Filed by Vifor (International) Ltd., St. Gallen (CH)
PCT Filed Nov. 12, 2020, PCT No. PCT/US2020/060112
§ 371(c)(1), (2) Date May 13, 2022,
PCT Pub. No. WO2021/097012, PCT Pub. Date May 20, 2021.
Claims priority of provisional application 62/935,218, filed on Nov. 14, 2019.
Prior Publication US 2023/0002306 A1, Jan. 5, 2023
Int. Cl. C07C 67/32 (2006.01); C08F 220/22 (2006.01); C08J 3/09 (2006.01)
CPC C07C 67/32 (2013.01) [C08F 220/22 (2013.01); C08J 3/095 (2013.01); C08J 2333/16 (2013.01)] 15 Claims
 
1. A process for preparing a fluoroacrylate compound comprising:
contacting a compound corresponding to the structure of Formula 1A with paraformaldehyde or formalin to form a reaction mixture of paraformaldehyde or formalin and a compound corresponding to the structure of Formula 1A

OG Complex Work Unit Chemistry
wherein each R1 group is independently alkyl or aryl; and
heating the reaction mixture in the presence of a base to form a fluoroacrylate compound corresponding to the structure of Formula 2A

OG Complex Work Unit Chemistry
wherein conversion of the compound corresponding to the structure of Formula 1A to the compound corresponding to the structure of Formula 2A occurs in the same reaction mixture or wherein the overall yield of the compound corresponding to the structure of Formula 2A is at least 75% based on the number of moles of the compound corresponding to the structure of Formula 1A; and
wherein the base comprises lithium carbonate, sodium carbonate, potassium carbonate, rubidium carbonate, cesium carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, or a combination thereof.