Iodine → HCID 13467546, compound

HRID 1193639Notes

Reaction equation

HRID 1193639 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.[C:12]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>CCOCC>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[OH:19])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 807IodineHCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 267314-BenzoylpyridineHCID 5462224Magnesium

Product 1

HCID 13467546HCID 13467546, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
25 °C

Procedure

To a suspension of 18.5 g (0.761 mole) of magnesium turnings and several crystals of iodine in 800 ml of anhydrous ether, cooled in an ice bath and under an atmosphere of argon was slowly added a solution of p-bromofluorobenzene in 200 ml of ether. The solution was stirred for 2 hr at 25° C. and 97.02 g (0.530 mole) of 4-benzoylpyridine was added as a solid. An additional 1 liter of anhydrous ether was added, and the solution was stirred at 25° C. for 3 hr. The reaction mixture was poured into an icy, aqueous solution of ammonium chloride. The mixture stood in the hood overnight and a white solid was collected. The solid was dissolved in a mixture of methanol-methylene chloride. The solution was filtered and the solvent was removed in vacuo. The residue was crystallized from chloroform-hexane to give 66.86 g (45%) of title compound as a white, crystalline solid, m.p. 189°-192° C. Part of this was recrystallized from methylene chloride-acetonitrile-hexane, m.p. 190°-192° C.

Workup

  1. temperaturecooled in an ice bath and under an atmosphere of argon
  2. stirringthe solution was stirred at 25° C. for 3 hr
  3. customstood in the hood overnight
  4. customa white solid was collected
  5. dissolutionThe solid was dissolved in a mixture of methanol-methylene chloride
  6. filtrationThe solution was filtered
  7. customthe solvent was removed in vacuo
  8. customThe residue was crystallized from chloroform-hexane

Sources & evidence

ORD record
ord-a8aaa4ce71864ff0be316d1e0c13cf67
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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