Diiodomethane → 1-Fluoro-4-iodo-2-nitrobenzene

HRID 606824Notes

Reaction equation

HRID 606824 reaction equation
N(OCCC(C)C)=O.[F:9][C:10]1[CH:15]=[CH:14][C:13](N)=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18].[I:20]CI>>[F:9][C:10]1[CH:15]=[CH:14][C:13]([I:20])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 145905821-Fluoro-4-iodo-2-nitrobenzeneYield 14%

Procedure

Add isoamyl nitrite (18.6 g, 160 mmol) to a suspension of 4-fluoro-3-nitrophenylamine (5.0 g, 32 mmol) in diiodomethane (150 mL). Stir under nitrogen at room temperature for 1 h. Heat at 70° C. for 1 h. Cool to room temperature and concentrate. Dilute with dichloromethane (500 mL) and water (100 mL). Collect the organic, concentrate and purify (silica gel chromatography, eluting with a gradient of 100:0 to 80:20 hexanes:ethyl acetate), to give the title compound as a yellow oil (1.22 g, 14%).

Workup

  1. temperatureHeat at 70° C. for 1 h
  2. temperatureCool to room temperature
  3. concentrationconcentrate
  4. additionDilute with dichloromethane (500 mL) and water (100 mL)
  5. customCollect the organic,
  6. concentrationconcentrate
  7. custompurify (silica gel chromatography
  8. washeluting with a gradient of 100:0 to 80:20 hexanes

Sources & evidence

ORD record
ord-d7711c2f277a415e9c058d6fe2a2a7ef
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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