Iodine → HCID 23455897, compound

HRID 262253Notes

Reaction equation

HRID 262253 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=3)[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[I:23]I>C1C=CC=CC=1>[I:23][C:3]1[O:4][C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=3)=[CH:7][C:6]=2[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 807IodineHCID 23455904HCID 23455904, compound

Product 1

HCID 23455897HCID 23455897, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.8 g. of the product of step B in 50 ml. of benzene is added 2.7 g. of iodine and 2.4 g. of mercuric oxide followed by stirring and heating at 60°-65° C. for about three days. The mixture is cooled and evaporated, and the residue is chromatographed on silica gel, eluting with a carbon tetrachloride-dichloromethane mixture, to provide ethyl 4-(2-iodo-3-methylbenzofuran-5-yl)phenylacetate. To this intermediate is added dichloromethane, then dinitrogen tetraoxide. After one hour the mixture is washed with water, then with sodium bisulfite solution and dried. Evaporation provides a residue which is recrystallized from a dichloromethane-hexane mixture to yield ethyl 4-(3-methyl-2-nitrobenzofuran-5-yl)phenylacetate.

Workup

  1. temperatureheating at 60°-65° C. for about three days
  2. temperatureThe mixture is cooled
  3. customevaporated
  4. customthe residue is chromatographed on silica gel
  5. washeluting with a carbon tetrachloride-dichloromethane mixture

Sources & evidence

ORD record
ord-71572b3d40a64ceeaddb5e72bcec9244
Source dataset
uspto-grants-1979_05
Patent number
US04153721

Reaction notes

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