Iodine → Methyl 3-iodo-4-methoxy-5-nitrobenzoate

HRID 852592Notes

Reaction equation

HRID 852592 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[I:17]I.N(OC(C)(C)C)=O>C1(C)C=CC=CC=1>[I:17][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 807IodineHCID 10906Tert-Butyl nitriteHCID 63022111Methyl 3-amino-4-(methyloxy)-5-nitrobenzoate

Product 1

HCID 69356091Methyl 3-iodo-4-methoxy-5-nitrobenzoateYield 96.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 3-amino-4-(methyloxy)-5-nitrobenzoate (D163) (370 mg, 1.64 mmol, 1 equiv) in toluene (20 ml) at 0° C. was added iodine (218 mg, 0.86 mmol, 0.5 equiv) then 1,1-dimethylethyl nitrite (200 mg, 1.75 mmol, 1.1 equiv) and the resulting mixture was stirred at room temperature for 15 h then partitioned between AcOEt and brine. The two layers were separated and the organic phase was dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel gave methyl 3-iodo-4-(methyloxy)-5-nitrobenzoate (D165) (280 mg, 51%) as a light brown solid. No molecular ion. RT=3.33 min.

Workup

  1. customthen partitioned between AcOEt and brine
  2. customThe two layers were separated
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-088853114f4744539a6364506dfee43c
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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