Water → alpha-Iodo-p-nitrotoluene

HRID 1271422Notes

Reaction equation

HRID 1271422 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[I-:12].[Na+].O>CC(C)=O>[I:12][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 74824-Nitrobenzyl chloride

Product 1

HCID 76598alpha-Iodo-p-nitrotolueneYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 1-chloromethyl-4-nitro-benzene (10 g, 58.3 mmol) and sodium iodide in acetone (150 ml) was refluxed for 1 h. Water was added until complete dissolution and the mixture extracted with ethyl acetate (4×100 ml). The combined organic layers were extracted with brine, dried over sodium sulfate and concentrated in vacuo yielding 13.9 g (95%) 1-Iodomethyl-4-nitro-benzene as beige crystals.

Workup

  1. temperaturewas refluxed for 1 h
  2. extractionthe mixture extracted with ethyl acetate (4×100 ml)
  3. extractionThe combined organic layers were extracted with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90f31404408c4179a87ff05d8e74e7dd
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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