Reaction #4608

Reaction equation

5-bromo-2-chloropyrimidine

4-amino-2-chlorophenol

potassium carbonate

dimethylsulfoxide

→

4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline

Yield 62.6%

Solvents

water

Conditions

Workup

1. 1
   Otherreacted in a nitrogen atmosphere at 120° C. for 1.5 hours
2. 2
   OtherAfter the completion of the reaction
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe extract was washed with water
5. 5
   Dryinga saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
6. 6
   Otherpurified by silica gel column chromatography

Procedure

Into a flask, 7.00 g of 5-bromo-2-chloropyrimidine, 5.19 g of 4-amino-2-chlorophenol, 9.98 g of potassium carbonate and 70 ml of dimethylsulfoxide were introduced, and reacted in a nitrogen atmosphere at 120° C. for 1.5 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 6.80 g of oily 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline was obtained.

Source