2-Benzyloxy-5-nitroiodobenzene → 4-(Benzyloxy)-3-iodobenzenamine

HRID 842039Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[I:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O.C(O)(=O)C.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[I:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -80 °C

Procedure

Iron powder (12.5 g, 224 mmol) was added to a suspension of 2-benzyloxy-5-nitroiodobenzene (10 g, 28 mmol) in water (300 ml) and acetic acid (75 ml) and the mixture was stirred at −80° C. for 12 hours. The mixture was allowed to cool to room temperature and filtered through Hyflo™, washing with 4:1 water:acetic acid and ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic extract was evaporated under reduced pressure. Saturated aqueous sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4), and the solvent was evaporated under reduced pressure to give the title compound as a brown oil (9 g, 99% yield). 1H NMR (360 MHz, CDCl3) δ 7.49-7.47 (2H, m), 7.40-7.28 (3H, m), 7.19 (1H, d, J 2.4 Hz), 6.70 (1H, d, J 8.6 Hz), 6.62 (1H, dd, J 2.4, 8.6 Hz), 5.04 (2H, s). MS (ES+) m/z 326 (M+H).

Workup

temperatureto cool to room temperature
filtrationfiltered through Hyflo™
washwashing with 4:1 water
extractionThe filtrate was extracted with ethyl acetate
extractionthe organic extract
customwas evaporated under reduced pressure
additionSaturated aqueous sodium hydrogen carbonate was added
extractionthe mixture was extracted with ethyl acetate
extractionThe organic extract
washwas washed with brine
dry with materialdried (MgSO4)
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-8d020c5621e64f8eb6ea154f6134c514
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06372754B1

Reaction notes

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