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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1691161Generated: October 27, 2026

Acetic Acid → 2-(2-Fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)pyridine

https://huagongshe.com/reaction/1691161

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantNitromethaneHCID 6375—
ReactantAmmonium AcetateHCID 517165—
Reactant3-Fluoro-4-(pyridin-2-ylmethoxy)-benzaldehydeHCID 59255224—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product2-(2-Fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)pyridineHCID 5925514190.4%

Reaction Conditions

Temperature110 °C

Reaction Steps

To an acetic acid (25.0 mL) solution of 3-fluoro-4-(pyridin-2-ylmethoxy)-benzaldehyde (2.80 g, 12.1 mmol) described in Manufacturing Example 87-1-1 were added nitromethane (3.69 g, 60.5 mmol) and ammonium acetate (1.87 g, 24.2 mmol) under nitrogen atmosphere at room temperature, which was stirred for 2 hours at 110° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.00 g) as a crude product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08153662B2
Source datasetuspto-grants-2012_04
ORD IDord-2ba73fb87db94c37814d84991cc0c0df
Source noteuspto-grants-2012_04