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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 406398Generated: October 30, 2026

Dimethylformamide → 5-(1-Fluorocyclopropyl)-2-methoxybenzaldehyde

https://huagongshe.com/reaction/406398

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium BicarbonateHCID 516892—
Reactant2-Bromo-4-(1-fluorocyclopropyl)-1-methoxybenzeneHCID 66633467—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
Product5-(1-Fluorocyclopropyl)-2-methoxybenzaldehydeHCID 86662655—

Reaction Conditions

Temperature-78 °C

Reaction Steps

n-Butyllithium (2.7M solution in hexane, 3.42 ml) was added at −78° C. to a solution of 2-bromo-4-(1-fluorocyclopropyl)-1-methoxybenzene (1.88 g) in THF (62 ml), followed by addition of a solution of DMF (650 μl) in THF. After the reaction mixture was stirred at −78° C. for 30 minutes, a saturated aqueous solution of sodium bicarbonate was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (1.00 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08754100B2
Source datasetuspto-grants-2014_06
ORD IDord-4375d25adb354f42be72c9add84c9f60
Source noteuspto-grants-2014_06