Diiodomethane → HCID 22647950, compound

HRID 394131Notes

Reaction equation

HRID 394131 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Br:10])[C:8]=1[CH3:9])N.C(ON=O)(C)(C)C.C(I)[I:19]>>[Br:1][C:2]1[CH:3]=[C:4]([I:19])[CH:6]=[C:7]([Br:10])[C:8]=1[CH3:9]

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 10906Tert-Butyl nitriteHCID 70157793,5-Dibromo-4-methylaniline

Product 1

HCID 22647950HCID 22647950, compound

Procedure

To a solution of 3,5-dibromo-4-methylaniline (4.17 g, 15.74 mmol) in CH2I2 (10 mL) was added tert-butylnitrite (3.0 mL, 23.61 mmol) slowly at 0° C. while stirring vigorously. The ice bath was removed and the reaction mixture was stirred at rt while the reaction was very exothermic, then placed it in a 80° C. oil bath and heated for 20 min. CH2I2 was distilled off under high vacuum, and the remaining residue was purified by flash chromatography eluting with 100% hexane to gave the title compound.

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction mixture was stirred at rt while the reaction
  3. customin a 80° C.
  4. temperatureheated for 20 min
  5. distillationCH2I2 was distilled off under high vacuum
  6. customthe remaining residue was purified by flash chromatography
  7. washeluting with 100% hexane

Sources & evidence

ORD record
ord-cb6ba0aab7554c1f97d1ccba81fd8f89
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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