Iodine → HCID 312935, compound

HRID 704331Notes

Reaction equation

HRID 704331 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].II.[C:11](#[N:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>O1CCCC1.[Zn].CCOCC.O>[NH2:18][C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

9

Reactant 4

HCID 807IodineHCID 7505BenzonitrileHCID 25517Ammonium ChlorideHCID 79040Ethyl 2-bromopropionate2×

Product 1

HCID 312935HCID 312935, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under vigorous agitation, 73.2 g of powdered electrolytic zinc were refluxed in 1.2 liter of anhydrous tetrahydrofuran and 10 ml of ethyl 2-bromopropionate were added together with a crystal of sublimed iodine. The reaction started and then, away from reflux, 40.8 ml of benzonitrile were added and the mixture was refluxed which was maintained by the slow addition of 58 ml of ethyl 2-bromopropionate. After cooling, the mixture was poured into 1.5 liters of water containing 200 g of ammonium chloride and extraction was done with ether. The extracts were washed with water, dried, and concentrated under reduced pressure. The residue was taken up with ether and the reduced pressure. The residue was taken up with ether and the insoluble matter was filtered off. The filtrate was concentrated under reduced pressure to obtain 76 g of an unstable product which was used rapidly for the next step.

Workup

  1. temperatureaway from reflux
  2. temperaturethe mixture was refluxed which
  3. temperatureAfter cooling
  4. washThe extracts were washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe insoluble matter was filtered off
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e82189e7542145cf88cf4ca90e9147f8
Source dataset
uspto-grants-1991_01
Patent number
US04987140

Reaction notes

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