Ethanol → (E)-ethyl 3-(4-chloro-3-fluorophenyl)acrylate

HRID 1774156Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[F:13].Cl[Si](C)(C)C.[CH2:19](O)[CH3:20]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:19][CH3:20])=[O:11])=[CH:4][C:3]=1[F:13]

Participants

Reactant 3

HCID 702Ethanol

HCID 6397Chlorotrimethylsilane

HCID 57084034-Chloro-3-fluorocinnamic acid

Product 1

HCID 86696656(E)-ethyl 3-(4-chloro-3-fluorophenyl)acrylateYield 99.65%

Procedure

(E)-3-(4-Chloro-3-fluorophenyl)acrylic acid (17.3 g, 86.24 mmol) was suspended in ethanol (200 mL), and chlorotrimethylsilane (24.00 mL, 189.7 mmol) was added. The mixture was then agitated for 20 hours and evaporated, to give (E)-ethyl 3-(4-chloro-3-fluorophenyl)acrylate (19.65 g, 85.94 mmol, 99.65% yield) as an oil, which solidified later.

Workup

customevaporated

Sources & evidence

ORD record: ord-00df0bfd79f54c35a47f69ed49d6f61a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09259470B2

Reaction notes

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