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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2283165Generated: October 31, 2026

Water → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde

https://huagongshe.com/reaction/2283165

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ReactantBromomethylcyclopropaneHCID 81503—
Reactant4-(Difluoromethoxy)-3-hydroxybenzaldehydeHCID 2758295—
SolventTetrahydrofuranHCID 8028—
Product3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehydeHCID 18973698—

Reaction Conditions

Temperature77.5 °C

Reaction Steps

4-Difluoromethoxy 3-hydroxy benzaldehyde in tetrahydrofuran (5 vol with respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was taken in a vessel and DBU (1.5 eq respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was added. To this first lot of cyclopropylmethylbromide (1.5 eq respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was added and heated to 75-80° C. After 2 hours second lot of cyclopropylmethyl bromide (0.5 eq with respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was added and maintained at 75-80° C. for 2 hours. To this third lot of cyclopropylmethyl bromide (0.5 eq with respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was added and maintained for 2 hours. The reaction mass was cooled to 20-25° C. and water was added. The reaction mixture was extracted with EtOAc and EtOAc extracts were washed with water. EtOAc was distilled out under reduced pressure at 40° C. to get 3-cyclopropylmethoxy 4-Difluoromethoxy benzaldehyde as brown oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09145365B2
Source datasetuspto-grants-2015_09
ORD IDord-a89a4979bf8a4ceeac5940a3c6fc1ec6
Source noteuspto-grants-2015_09