Iodine → 2-Bromo-1-iodo-3-(trifluoromethyl)benzene

HRID 1422609Notes

Reaction equation

HRID 1422609 reaction equation
N([O-])=O.[Na+].[Br:5][C:6]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][C:7]=1N.OS(O)(=O)=O.[I:22]I.[O-]S([O-])=O.[Na+].[Na+]>O>[Br:5][C:6]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][C:7]=1[I:22]

Participants

7

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 24437Sodium SulfiteHCID 940582-Bromo-3-(trifluoromethyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 534844702-Bromo-1-iodo-3-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
40 °C

Procedure

An ice-cold solution of NaNO2 (0.15 g) in water (0.5 mL) is added to a mixture of 2-bromo-3-trifluoromethyl-aniline (0.48 g), concentrated H2SO4 (2 mL), and water (1.8 mL) at ca. 5° C. The mixture is stirred in the cooling bath for 20 min and then poured into a solution of KI (0.56 g) and I2 (0.56 g) in water (0.5 mL). After gas evolution ceases, the mixture is heated to 40° C. and stirred at this temperature for 1 h. The mixture is cooled to room temperature and aqueous Na2SO3 solution is added. The resulting mixture is extracted with ethyl acetate, and the combined extracts are dried (Na2SO4) and concentrated. The solvent is evaporated and the residue is chromatographed (cyclohexane/ethyl acetate 95:5→90:10) to give the title compound.

Workup

  1. stirringstirred at this temperature for 1 h
  2. temperatureThe mixture is cooled to room temperature
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. dry with materialthe combined extracts are dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed (cyclohexane/ethyl acetate 95:5→90:10)

Sources & evidence

ORD record
ord-381a02c6b88d4df79d9454cce2a87247
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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