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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2097463Generated: October 30, 2026

Dimethylformamide → 4-Bromo-2-cyclobutoxy-1-methoxymethoxybenzene

https://huagongshe.com/reaction/2097463

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
ReactantBromocyclobutaneHCID 78110—
ReactantHCID 57256524HCID 57256524—
SolventWaterHCID 962—
Product4-Bromo-2-cyclobutoxy-1-methoxymethoxybenzeneHCID 6660265666%

Reaction Conditions

Temperature100 °C

Reaction Steps

To 10 ml of N,N-dimethylformamide solution containing 1.73 g (7.4 mmol) of 5-bromo-2-methoxymethoxyphenol obtained in Reference Example 5-(b) were added 1.0 g (7.2 mmol) of potassium carbonate and 1.0 g (7.4 mmol) of cyclobutyl bromide, and the mixture was stirred at 100° C. for 5 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 1.4 g of the title compound as a colorless oil. (Yield: 66%)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08450319B2
Source datasetuspto-grants-2013_05
ORD IDord-ff9ca79b9b274449971d161d0a1583de
Source noteuspto-grants-2013_05