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

HRID 471458Notes

Reaction equation

[Br:1][C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:3]=1N.OS(O)(=O)=O.N([O-])=O.[Na+].[I-:22].[K+].II.[O-]S([O-])=O.[Na+].[Na+]>O>[Br:1][C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:3]=1[I:22]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Bromo-3-trifluoromethylaniline (8 g, 33.33 mmol) is suspended in water (90 mL) and cooled to 0° C. 96% H2SO4 (26.7 mL, 13.7 mmol) is added and the mixture stirred for 30 minutes. NaNO2 (2.41 g, 35 mmol) is dissolved in a small quantity of water and added dropwise at 0° C. The mixture is stirred for 30 minutes then potassium iodide (9.24 g, 55.66 mmol) and iodine (9.31 g, 36.66 mmol) in water are added dropwise with cooling. The mixture is stirred until gas evolution ceases then warmed to 40° C. and allowed to cool to room temperature. The mixture is shaken with excess aqueous Na2SO3 solution and extracted with ethyl acetate. The organic extracts are evaporated and the residue purified by flash chromatography (eluent: cyclohexane) to give the title compound (Yield 10.0 g)

Workup

additionadded dropwise at 0° C
stirringThe mixture is stirred for 30 minutes
temperaturewith cooling
stirringThe mixture is stirred until gas evolution ceases
temperaturethen warmed to 40° C.
temperatureto cool to room temperature
extractionextracted with ethyl acetate
customThe organic extracts are evaporated
customthe residue purified by flash chromatography (eluent: cyclohexane)

Sources & evidence

ORD record: ord-a6e6edc46afe4276bf509ccdc0aa1228
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633182B2

Reaction notes

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