Bromine → HCID 178503448, compound

HRID 396363Notes

Reaction equation

HRID 396363 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-pyrimidinyl)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-4fd86915d04c4b24aff7ac64595da735
Source dataset
uspto-grants-2003_08
Patent number
US06608072B1

Reaction notes

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