191602-52-5 → HCID 18787114, compound

HRID 1107283Notes

Reaction equation

HRID 1107283 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-])=O)[CH:3]=1>C(O)(=O)C.O.[Fe]>[NH2:11][C:4]1[CH:3]=[C:2]([Br:1])[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=1

Participants

5

Reactant 1

HCID 18787034191602-52-5

Product 1

HCID 18787114HCID 18787114, compoundYield 74.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

7-Bromo-5-nitro-2,3-dihydrobenzofuran (2 g) was suspended in acetic acid (5 ml) and water (12 ml). Iron powder (3.5 g) was added and the mixture was heated at reflux for 3hr. The cooled mixture was cooled and filtered through celite. The filtrate was concentrated and azeotroped with toluene. The residue was purified by chromatography on silica using 10% ethyl acetate in hexane as eluent to afford the title compound (1.3 g) as an oil. 1H NMR (250 MHz, CDCl3) δ 3.22 (2H, t, J=7.5 Hz), 3.38 (2H, br s), 4.58 (2H, t, J=8 Hz), 6.51-6.53 (1H, m), 6.63-6.64 (1H, m).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3hr
  3. temperatureThe cooled mixture was cooled
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated
  6. customazeotroped with toluene
  7. customThe residue was purified by chromatography on silica using 10% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-1e4f8a0da8514f27a0ef2c8064418f22
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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