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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 629424Generated: October 27, 2026

Sodium Carbonate → 2-fluoro-N-methyl-4-vinylbenzamide

https://huagongshe.com/reaction/629424

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 5233012—
ReactantBenzamide, 4-bromo-2-fluoro-N-methyl-HCID 24694329—
Solvent1,2-DimethoxyethaneHCID 8071—
Product2-fluoro-N-methyl-4-vinylbenzamideHCID 118468329119.8%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 4-bromo-2-fluoro-N-methylbenzamide (0.80 g), vinylboronic acid pinacol cyclic ester (0.80 g) and 2M aqueous sodium carbonate solution (3.45 mL) in DME (17.3 mL) was argon-purged. Bis(triphenylphosphine)palladium(II) dichloride (0.12 g) was added thereto, and the mixture was stirred overnight at 80° C. The reaction solution was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to short silica gel column chromatography, and the solvent was evaporated under reduced pressure to give the title compound (0.74 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09315458B2
Source datasetuspto-grants-2016_04
ORD IDord-2f010bc452bc4c7d8d98891fce9354b7
Source noteuspto-grants-2016_04