Iodine → HCID 117737295, compound

HRID 1504476Notes

Reaction equation

HRID 1504476 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[I:12]I>FC(F)(F)S([O-])(=O)=O.[Ag+].C(Cl)Cl>[Br:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([I:12])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 807Iodine2×HCID 112180922-Bromo-4-methoxybenzonitrile

Product 1

HCID 117737295HCID 117737295, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A RBF was charged with 2-bromo-4-methoxybenzonitrile (891 mg, 4.20 mmol, Matrix Scientific) and DCM (1.68E+04 μl) to give a clear solution. silver trifluoromethanesulfonate (1188 mg, 4.62 mmol) and iodine (1173 mg, 4.62 mmol) were added in sequence. The resulting mixture was stirred for 2 d. Additional portions of silver trifluoromethanesulfonate (1188 mg, 4.62 mmol) and iodine (1173 mg, 4.62 mmol) were added, and the mixture was stirred for another 5 h. The reaction mixture was then filtered through celite with the aid of DCM. The filtrate was shaken with saturated aq. sodium thiosulfate until the color disappeared. The biphasic mixture was diluted with water then the layers were separated. The aq. layer was extracted with DCM (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 25-g silica gel column, 5-30% EtOAc/Heptane) give 2-bromo-5-iodo-4-methoxybenzonitrile (811 mg, 2.400 mmol, 57.1% yield) as an off-white solid. m/z (ESI) 337.8 (M+H)+.

Workup

  1. customto give a clear solution
  2. stirringthe mixture was stirred for another 5 h
  3. filtrationThe reaction mixture was then filtered through celite with the aid of DCM
  4. stirringThe filtrate was shaken with saturated aq. sodium thiosulfate until the color
  5. additionThe biphasic mixture was diluted with water
  6. customthe layers were separated
  7. extractionThe aq. layer was extracted with DCM (2×)
  8. dry with materialThe combined organic extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 25-g silica gel column, 5-30% EtOAc/Heptane)

Sources & evidence

ORD record
ord-66ddfa6b86264cc7aee5e9f765e29dbf
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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