191602-52-5 → HCID 18787114, compound
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]=1Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
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
- temperaturethe mixture was heated
- temperatureat reflux for 3hr
- temperatureThe cooled mixture was cooled
- filtrationfiltered through celite
- concentrationThe filtrate was concentrated
- customazeotroped with toluene
- 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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