Acetic Acid → HCID 70200667, compound

HRID 342442Notes

Reaction equation

HRID 342442 reaction equation
[Br:1][C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[C:4]=2[O:5][C:6]=1[CH3:7].C(O)(=O)C>C(O)C.O1CCOCC1.[Fe]>[NH2:12][C:8]1[C:4]2[O:5][C:6]([CH3:7])=[C:2]([Br:1])[C:3]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 12264720HCID 12264720, compound

Product 1

HCID 70200667HCID 70200667, compoundYield 98.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-bromo-2-methyl-7-nitrobenzo[b]furan (300 mg) and acetic acid (776 mg) in a mixture of ethanol (6 ml) and dioxane (1.5 ml) was added iron (722 mg) at 50° C. The mixture was refluxed for 1.5 hours and the insoluble material was filtered off. The filtratate was evaporated in vacuo with toluene. The residue was extracted with a mixture of ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated and it was extracted with ethyl acetate from aqueous layer. The organic layer was combined and washed with saturated aqueous sodium bicarbonate, brine, dried over sodium sulfate, and evaporated in vacuo to give 7-amino-3-bromo-2-methylbenzo[b]furan (262 mg) as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. filtrationthe insoluble material was filtered off
  3. customThe filtratate was evaporated in vacuo with toluene
  4. extractionThe residue was extracted with a mixture of ethyl acetate and saturated aqueous sodium bicarbonate
  5. customThe organic layer was separated
  6. extractionit was extracted with ethyl acetate from aqueous layer
  7. washwashed with saturated aqueous sodium bicarbonate, brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-b2e89716ca8c40abb3c7971749de5d54
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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