Bromine → 2-Bromo-2-[2-(methylthio-4-pyrimidinyl)]-1-phenylethanone

HRID 2212869Notes

Reaction equation

HRID 2212869 reaction equation
[Br:1]Br.[CH3:3][S:4][C:5]1[N:10]=[C:9]([CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[CH:8]=[CH:7][N:6]=1>C(O)(=O)C>[Br:1][CH:11]([C:9]1[CH:8]=[CH:7][N:6]=[C:5]([S:4][CH3:3])[N:10]=1)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

4

Reactant 2

HCID 24408Bromine3×HCID 129858292-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-phenylethan-1-one

Product 1

HCID 129858302-Bromo-2-[2-(methylthio-4-pyrimidinyl)]-1-phenylethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (24.1 g, 0.15 mol) is added with stirring to 2-(2-methylthio-pyrimidin-4-yl)-1-phenyl-ethanone (36.8 g, 0.15 mol) in acetic acid (300 ml) in such a way that the reaction temperature does not exceed +25° C. and the color of the bromine is discharged immediately. After the addition of the bromine solution the solvent is removed by evaporation under vacuum. The pH of the resulting oil is adjusted to 8 using an aqueous saturated sodium bicarbonate solution and the product is extracted several times with diethylther. Drying the combined extracts with magnesium sulfate, filtering and evaporation of the solvent gives the crude 2-bromo-2-(2-methylthio-pyrimidin-4-yl)-1-phenyl-ethanone in form of an oil of sufficient purity for the following step.

Workup

  1. customdoes not exceed +25° C.
  2. customis removed by evaporation under vacuum
  3. extractionthe product is extracted several times with diethylther
  4. dry with materialDrying the combined extracts with magnesium sulfate
  5. filtrationfiltering
  6. customevaporation of the solvent

Sources & evidence

ORD record
ord-7247a1ba44ba47bda4393e8b1fbc9a89
Source dataset
uspto-grants-2006_09
Patent number
US07105517B2

Reaction notes

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