2,3,5-Trifluorophenylboronic Acid → 4-iodo-1-(2,3,5-trifluorophenyl)-1H-imidazole

HRID 1898641Notes

Reaction equation

HRID 1898641 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][C:3]=1B(O)O.[I:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1>CO>[I:13][C:14]1[N:15]=[CH:16][N:17]([C:3]2[CH:4]=[C:5]([F:9])[CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH:18]=1

Participants

4

Reactant 2

HCID 40788432,3,5-Trifluorophenylboronic AcidHCID 178506559HCID 178506559, compound

Product 1

HCID 575166554-iodo-1-(2,3,5-trifluorophenyl)-1H-imidazoleYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that outlined in Synthesis 2008, 795-799: A mixture of 2,3,5-trifluorophenylboronic acid (0.302 g, 1.72 mmol), 4-iodo-1H-imidazole (0.498 g, 2.57 mmol), 2 mL of methanol, and Cu2O (0.049 g, 0.34 mmol) was stirred under air for 21 h, then filtered through Celite and concentrated to an oily white solid. Column chromatography (0->33% EtOAc/hexanes) afforded 0.150 g (27%) of 4-iodo-1-(2,3,5-trifluorophenyl)-1H-imidazole as a white solid. MS: (M+H)+=325.

Workup

  1. customthat outlined in Synthesis 2008, 795-799
  2. filtrationfiltered through Celite
  3. concentrationconcentrated to an oily white solid

Sources & evidence

ORD record
ord-74dcab92a26c4b78ae3468d38c87054e
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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