Bromine → HCID 178503448, compound

HRID 1369409Notes

Reaction equation

HRID 1369409 reaction equation
[Br:1]Br.[F:3][C:4]1([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])[CH:9]=[CH:8][N:7]=[C:6]([S:10][CH3:11])[NH:5]1>C(O)(=O)C>[F:3][C:4]1([CH:12]([Br:1])[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])[CH:9]=[CH:8][N:7]=[C:6]([S:10][CH3:11])[NH:5]1

Participants

4

Reactant 2

HCID 24408BromineHCID 178503449HCID 178503449, compound

Product 1

HCID 178503448HCID 178503448, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (1.22 g, 7.6 mmol) in acetic acid (5.6 ml) is added to a solution of 4-Fluoro-2-(2-methylthio-4-pyrimidyl)acetophenone (2 g; 7.6 mmol) in acetic acid (40 ml. The initially thick precipitate is almost dissolved after 20 min, filtered and the filtrate evaporated to dryness. The residue is taken up in a saturated solution of NaHCO3 and extracted three times with tert.butyl methyl ether. The combined organic phases are dried over Na2SO4 and evaporated to dryness to yield 2.6 g (100%) of a brown oil, which is used in the next step without purification.

Workup

  1. dissolutionThe initially thick precipitate is almost dissolved after 20 min
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness
  4. extractionextracted three times with tert.butyl methyl ether
  5. dry with materialThe combined organic phases are dried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-7550c33b86d94462955b06af020cb54a
Source dataset
uspto-grants-2003_06
Patent number
US06579874B2

Reaction notes

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