2-Fluoro-4-(trifluoromethyl)benzaldehyde → 2-Fluoro-4-(trifluoromethyl)cinnamic acid

Reaction equation

CS(OC1C=CC(/C=[CH:13]/[C:14]([OH:16])=[O:15])=CC=1)(=O)=O.[F:17][C:18]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:19]=1[CH:20]=O.C(C1C=CC(OS(C)(=O)=O)=CC=1)=O>>[F:17][C:18]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:19]=1/[CH:20]=[CH:13]/[C:14]([OH:16])=[O:15]

Participants

Reactant 3

HCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehyde

HCID 144212934-Formylphenyl methanesulfonate

HCID 15726601(2E)-3-(4-((Methylsulfonyl)oxy)phenyl)-2-propenoic acid

Product 1

HCID 57096462-Fluoro-4-(trifluoromethyl)cinnamic acid

Procedure

5.12 g of (E)-2-Fluoro-4-(trifluoromethyl)cinnamic acid were synthesized as described for (E)-3-(4-(methanesulfonyloxy)phenyl)acrylic acid using 2-fluoro-4-trifluoromethylbenzaldehyde (commercially available from Aldrich) instead of methanesulfonic acid 4-formylphenyl ester.

Sources & evidence

ORD record: ord-240fde7c4bb840ab8df31cec2fff2f65
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101898B2

Reaction notes

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