Nitric Acid → Ethyl 4-iodo-3-nitrobenzoate

HRID 40056Notes

Reaction equation

HRID 40056 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)[CH3:2].[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[I:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:12])=[CH:6][C:7]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 142891Ethyl 4-iodobenzoate

Product 1

HCID 11186300Ethyl 4-iodo-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of ethyl-4-iodobenzoate ( 10.0 g, 36.2 mmol) in H2SO4 (20 ml) at 0° C. was added dropwise HNO3 ( 4.7 ml, 72.4 mmol). Reaction was stirred at room temperature for 1 h, cooled to 0° C., quenched with ice, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, concentrated in vacuo to yield the crude title compound as a yellow solid.

Workup

  1. customReaction
  2. temperaturecooled to 0° C.
  3. customquenched with ice
  4. additiondiluted with EtOAc
  5. washwashed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b1a7fe1cb964c09a493b515c69f2e2a
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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