Trifluoroacetic acid → HCID 58415249, compound

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

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).