Trifluoromethanesulfonic acid → 1-Chloro-2,5-difluoro-4-iodobenzene

HRID 1916419Notes

Reaction equation

HRID 1916419 reaction equation
FC(F)(F)S(O)(=O)=O.[Cl:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[F:17].[I:18]N1C(=O)CCC1=O>>[Cl:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([I:18])=[CH:12][C:11]=1[F:17]

Participants

4

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 1375611-Chloro-2,5-difluorobenzene

Product 1

HCID 510000881-Chloro-2,5-difluoro-4-iodobenzeneYield 77.5%

Conditions

Temperature
0 °C

Procedure

Trifluoromethanesulfonic acid (9.9 mL, 110 mmol) was added to 2-chloro-1,4-difluorobenzene (2.2 g, 15 mmol) at room temperature and then cooled to 0° C. N-Iodosuccinimide (3.16 g, 14.1 mmol) was then added in multiple portions. After 10 minutes, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction mixture was poured over ice-water and extracted with hexane. The organic layer was washed with saturated Na2SO4, dried and concentrated. The crude product was purified by silica gel chromatography (100% hexanes) to give 1-chloro-2,5-difluoro-4-iodobenzene (3.0 g, 74%). 1H NMR (400 MHz, CDCl3) δ 7.52 (dd, J=5.4, 7.8, 1H), 7.17-7.08 (m, 1H).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with hexane
  3. washThe organic layer was washed with saturated Na2SO4
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography (100% hexanes)

Sources & evidence

ORD record
ord-01a6d53bfcbb42f38dd45af3b2420292
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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