Methyl Acrylate → HCID 123194218, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8](I)=[CH:7][C:4]=1[CH:5]=[O:6].[C:12]([O:16]C)(=[O:15])[CH:13]=[CH2:14]>>[CH:5]([C:4]1[CH:7]=[C:8]([CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[CH:14]=[CH:13][C:12]([OH:16])=[O:15])=[O:6]Participants
Procedure
In order to implement this procedure, 2-methoxy-5-iodobenzaldehyde (V) was used as starting material, which, through a Heck-type reaction with methyl acrylate followed by in situ hydrolysis of the ester gave 3-formyl-4-methoxycinnamic acid (VI). Alternatively, the coupling reaction may be carried out with acrylic acid, therefore avoiding the hydrolysis step. The 3-formyl-4-methoxycinnamic acid (VI) was reacted with 3 equivalents of Deoxo-Fluor® solution in toluene or tetrahydrofuran, preferably Deoxo-Fluor® 50% in toluene. Dichloromethane the is the preferred reaction solvent between 0° and a reflux temperature, preferably 250. Upon completion of the reaction (determined by thin-layer chromatography) the mixture is diluted with dichloromethane and percolated through a silica gel bed under an inert atmosphere to remove the by-products from the fluorination reaction, giving a solution of 3-difluoromethyl-4-methoxy cinnamyl fluoride (VII).
Sources & evidence
- ORD record
- ord-5e7749b03a224f92b556643792f82e49
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255071B2
Reaction notes
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