Methane, tetraiodo- → HCID 86708460, compound

HRID 921614Notes

Reaction equation

HRID 921614 reaction equation
C(I)(I)(I)I.[Br:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([N+:18]([O-])=O)[C:16]=1[Cl:17])[C:10]([O:12][CH3:13])=[O:11]>CC(O)=O.[Fe]>[NH2:18][C:15]1[CH:14]=[C:9]([CH:8]=[C:7]([Br:6])[C:16]=1[Cl:17])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 2

HCID 10487Methane, tetraiodo-HCID 81430882HCID 81430882, compound

Product 1

HCID 86708460HCID 86708460, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

(I4C): Fe powder (2.84 g, 50.9 mmol) was added to a solution of methyl 3-bromo-4-chloro-5-nitrobenzoate (5 g, 16.98 mmol) in AcOH (29.3 ml). The suspension was heated to 60° C. 1 h. The vessel was cooled to room temperature and then AcOH was removed via rotovap. The residue was placed in a 1 L beaker and was carefully neutralized with saturated sodium bicarbonate. The precipitate was removed via filtration through Celite and the filtrate was extracted with EtOAc. The organics were combined, washed with water and brine, and then dried over sodium sulfate. Filtration and concentration afforded methyl 3-amino-5-bromo-4-chlorobenzoate (4.19 g)) as a yellow solid.

Workup

  1. custom1 h
  2. temperatureThe vessel was cooled to room temperature
  3. customAcOH was removed via rotovap
  4. customThe precipitate was removed via filtration through Celite
  5. extractionthe filtrate was extracted with EtOAc
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-4e224002b518484692c675551c50329b
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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