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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 231805Generated: October 26, 2026

Dimethyl Sulfoxide → 4-(5-Bromo-2-pyrimidinyloxy)-3-chloroaniline

https://huagongshe.com/reaction/231805

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfoxideHCID 679—
ReactantPotassium CarbonateHCID 11430—
Reactant4-Amino-2-chlorophenolHCID 77578—
Reactant5-Bromo-2-chloropyrimidineHCID 606665—
SolventWaterHCID 962—
Product4-(5-Bromo-2-pyrimidinyloxy)-3-chloroanilineHCID 1377144078.9%

Reaction Steps

Into a flask, 10.0 g of 5-bromo-2-chloropyrimidine, 7.42 g of 4-amino-2-chlorophenol, 14.26 g of potassium carbonate and 100 ml of dimethylsulfoxide were introduced, and reacted in a nitrogen atmosphere at 120° C. for 2.5 hours under stirring. After the completion of the reaction, the product was poured into water, and extracted with ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and then purified by silica gel column chromatography, whereby 12.26 g of oily 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04849425
Source datasetuspto-grants-1989_07
ORD IDord-645192e7bb7a41fab9f7bdf223253c89
Source noteuspto-grants-1989_07