Sulfuric Acid → 1-Iodo-4-nitro-2-(trifluoromethyl)benzene

HRID 54396

Reaction equation

HRID 54396 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].OS(O)(=O)=O.N([O-])=O.[Na+].[Na+].[I-:25]>O>[I:25][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5238Sodium IodideHCID 671284-Nitro-alpha,alpha,alpha-trifluoro-o-toluidineHCID 23668193Sodium Nitrite

Product 1

HCID 192617781-Iodo-4-nitro-2-(trifluoromethyl)benzeneYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 3.1 g (15.0 mmol) of 2-amino-5-nitrobenzotrifluoride in 60 mL of 40% (v/v) H2SO4 stirred in an ice-bath was added dropwise a solution of 2.1 g (30.4 mmol) of NaNO2 in 10 mL of H2O. The resulting yellow solution was stirred in an ice-bath for 1 h and it was added dropwise into a well stirred solution of 10 g of NaI in 250 mL of H2O cooled in an ice bath. Gas releasing and precipitate was observed. The mixture was stirred overnight at 25° C., filtered and washed by water, and dried to leave pale yellow solid (4.5 g, 94%), mp 81°-82° C. 1H NMR (CDCl3), 8.047 (dd, 1), 8.272 (d, 1), 8.483 (d, 1).

Workup

  1. stirringThe resulting yellow solution was stirred in an ice-bath for 1 h
  2. additionit was added dropwise into a well
  3. temperaturecooled in an ice bath
  4. stirringThe mixture was stirred overnight at 25° C.
  5. filtrationfiltered
  6. washwashed by water
  7. customdried

Sources & evidence

ORD record
ord-927e014c875c4451a486c552d6849f30
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Linked notes

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