Iodine → HCID 23036403, compound

HRID 1193667Notes

Reaction equation

HRID 1193667 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.[O:12]([CH2:19][CH2:20][CH2:21][N:22]1[CH2:32][CH2:31][CH:25]([C:26]([O:28]CC)=O)[CH2:24][CH2:23]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+].[C:35]([OH:40])(=[O:39])[C:36]([OH:38])=[O:37]>O1CCCC1.CO>[C:35]([OH:40])(=[O:39])[C:36]([OH:38])=[O:37].[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:26]([C:36]2[CH:35]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)([CH:25]2[CH2:24][CH2:23][N:22]([CH2:21][CH2:20][CH2:19][O:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:32][CH2:31]2)[OH:28])=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 807IodineHCID 971Oxalic AcidHCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 6459735HCID 6459735, compound

Product 1

HCID 23036403HCID 23036403, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of 5.10 g (0.21 mole) of magnesium turnings and a crystal of iodine in 800 ml of dry tetrahydrofuran (distilled from lithium aluminum hydride) was added a solution of 36.75 g (0.21 mole) of p-bromofluorobenzene in 100 ml of tetrahydrofuran. The reaction flask was cooled in an ice bath during this addition, and the reaction mixture was under an atmosphere of nitrogen. The mixture was stirred at ambient temperature for 1 hr. A solution of 20.17 g (0.0693 mole) of ethyl N-(3-phenoxypropyl)isonipecotate in 100 ml of tetrahydrofuran was added and the solution was stirred at room temperature for 16 hr. The mixture was poured into an icy solution of ammonium chloride and the aqueous mixture was extracted with methylene chloride. The methylene chloride solution was extracted with dilute sodium hydroxide and was dried over magnesium sulfate. The solvent was removed in vacuo to give a gummy residue. The residue was treated with a solution of oxalic acid in methanol and the salt was recrystallized from methanol-ether to give 24.17 g (66.2%) of white crystalline solid, m.p. 153°-155° C.

Workup

  1. temperatureThe reaction flask was cooled in an ice bath during this addition
  2. stirringthe solution was stirred at room temperature for 16 hr
  3. extractionthe aqueous mixture was extracted with methylene chloride
  4. extractionThe methylene chloride solution was extracted with dilute sodium hydroxide
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give a gummy residue
  8. customthe salt was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-af79d8b90d844e4596af4cf14d457c3a
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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