Hydrochloric Acid → HCID 19761595, compound

HRID 1033763Notes

Reaction equation

HRID 1033763 reaction equation
Cl.[I:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1>O.C(O)C.[Fe]>[I:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 122932821-Iodo-4-(4-nitrophenoxy)benzene

Product 1

HCID 19761595HCID 19761595, compoundYield 95.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 6.04 ml (68.4 mmole) of concentrated hydrochloric acid in 25 ml of water and 25 ml of ethanol was added in a dropwise manner over 50 minutes to a mechanically stirred refluxing suspension of 23.34 g (68.4 mmole) of 4-(4'-iodophenoxy) nitrobenzene and 11.46 g (205 mmole, 3.0 equiv) of iron filings in 150 ml of water and 150 ml of ethanol. After 1 hour, the mixture was allowed to cool to room temperature and was evaporated to about 200 ml volume. The mixture was made alkaline to a pH of about 11 using 10% aqueous sodium hydroxide solution before adding 200 ml of water and 250 ml of ethyl acetate. The aqueous fraction was extracted twice with 50 ml of ethyl acetate and the combined organic phase was washed twice with 125 ml of water and 50 ml of brine, dried over MgSO4, filtered and evaporated to obtain 20.25 g of the desired product as a brown semi solid. Flash column chromatography (0-10% EtOAc/CH2Cl2 eluent) yielded 13.40 g (62.9%) of the product as pale brown crystals.

Workup

  1. temperaturerefluxing
  2. customwas evaporated to about 200 ml volume
  3. additionbefore adding 200 ml of water and 250 ml of ethyl acetate
  4. extractionThe aqueous fraction was extracted twice with 50 ml of ethyl acetate
  5. washthe combined organic phase was washed twice with 125 ml of water and 50 ml of brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-be7d0d2f8047482c8c2028b4169871bd
Source dataset
uspto-grants-1994_05
Patent number
US05312830

Reaction notes

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