Iodine → 1-Iodo-2-methyl-4-(trifluoromethyl)benzene

HRID 2093179Notes

Reaction equation

HRID 2093179 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1N.N(OCCCCC)=O.[I:21]I>C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[I:21]

Participants

6

Reactant 3

HCID 807IodineHCID 10026Pentyl nitriteHCID 137504374-Amino-3-methylbenzotrifluoride

Product 1

HCID 210779091-Iodo-2-methyl-4-(trifluoromethyl)benzene

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4-trifluoromethyl aniline (Step A) (2.2 g, 12.6 mmol) in chloroform (20 ml) at room temperature were added n-pentyl nitrite (2.2 g, 18.9 mmol) and iodine (6.38 g, 25.1 mmol). The mixture was heated to reflux for 1 h. The mixture was diluted with methylene chloride (50 ml). The solution was washed with saturated aqueous sodium thiosulfate, brine and dried over sodium sulfate. The title compound was obtained after flash column using hexane as the eluant.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. washThe solution was washed with saturated aqueous sodium thiosulfate, brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-8a2ba375fa3f47bd81c97aac3412c86f
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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