Trifluoroacetic acid → HCID 58415249, compound

HRID 2075227Notes

Reaction equation

HRID 2075227 reaction equation
[B-](F)(F)(F)F.C1C=CN=CC=1.C1C=CN=CC=1.[IH2+:18].[CH3:19][O:20][C:21]1[CH:33]=[CH:32][C:24]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:23][CH:22]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:18][C:33]1[CH:32]=[C:24]([CH:23]=[CH:22][C:21]=1[O:20][CH3:19])[CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10883201Bis(pyridine)iodonium tetrafluoroborateHCID 235532633-[(4-Methoxyphenyl)methyl]pyridine

Product 1

HCID 58415249HCID 58415249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis(pyridine)iodonium tetrafluoroborate (1.35 g, 3.64 mmol) was added to a solution of 3-(4-methoxybenzyl)pyridine (720 mg, 3.64 mmol) in 9:1 TFA:DCM (20 mL) and the mixture was stirred for 1 h at 0° C. The ice bath was removed and the reaction was stirred for 2 h. EtOAc was added and the mixture was washed with water twice, satd. sodium thiosulfate twice, dried over MgSO4, concentrated in vacuo, and purified by column chromatography to give 3-(3-iodo-4-methoxybenzyl)pyridine as a yellow oil. MS (ESI) m/z: Calculated: 325.0; Observed: 326.3 (M++1).

Workup

  1. customThe ice bath was removed
  2. additionEtOAc was added
  3. washthe mixture was washed with water twice
  4. dry with materialsodium thiosulfate twice, dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-0579b92390174d34801aae2d489b4f63
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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