Water → 2-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-imidazole

HRID 1473361Notes

Reaction equation

HRID 1473361 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[Sn](CCCC)(CCCC)CCCC.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1I.[F-].[K+].O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][C:26]=1[C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 27632521-Methyl-2-(tributylstannyl)-1H-imidazoleHCID 467352311-Bromo-2-iodo-4-(trifluoromethyl)benzene

Product 1

HCID 866874082-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-imidazoleYield 64.6%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of PdCl2(dppf)-CH2Cl2 adduct (0.233 g, 0.285 mmol), 1-methyl-2-(tributylstannyl)imidazole (2.189 ml, 6.84 mmol), 1-bromo-2-iodo-4-(trifluoromethyl)benzene (0.919 ml, 5.70 mmol), and potassium fluoride (1.656 g, 28.5 mmol) in 6 mL DMF was heated to 80° C. overnight. LC/MS showed product, so the reaction mixture was poured into water and was extracted with DCM. The organics were dried over MgSO4 and concentrated. Purification of the crude residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 2-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-imidazole (1.122 g, 3.68 mmol, 64.5% yield). m/z (ESI) 307.2 (M+H)+.

Workup

  1. extractionwas extracted with DCM
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customPurification of the crude residue by silica gel column chromatography (0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-4c79b97521bf4dbaa0dbc838e75f0a0e
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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