4-Fluoroiodobenzene → 1-(4-fluorophenyl)-3-(2-hydroxyethyl)-2(3H)-benzimidazolone

HRID 1290786Notes

Reaction equation

HRID 1290786 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13].[F:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-]>[O-2].[Zn+2].O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:6]2[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:4]([CH2:3][CH2:2][OH:1])[C:5]2=[O:13])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 96054-FluoroiodobenzeneHCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 41574231-(2-Hydroxyethyl)-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 232826611-(4-fluorophenyl)-3-(2-hydroxyethyl)-2(3H)-benzimidazoloneYield 14.5%

Reagents, catalysts & solvents 2

HCID 3007857Zinc OxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-(2-hydroxyethyl)benzimidazolone (J. Davoll, J. Chem. Soc., 1960, 308) (9 g), 4-fluoroiodobenzene (23 g), potassium carbonate (8.0 g), cupper(I) iodide (1 g), and zinc oxide (0.5 g) in N-methyl-2(3H)-pyrrolidinone (100 ml) was kept at 155° C. for 4.5 h. After cooling water (500 ml) was added followed by extraction with ethyl acetate (3×200 ml). The organic phase was washed with water and saturated calcium chloride solution and dried over magnesium sulfate. Removal of solvent in vacuo gave an oil which was purified by chromatography (silica gel, ethyl acetate) giving 1-(4-fluorophenyl)-3-(2-hydroxyethyl)-2(3H)-benzimidazolone (2 g) as a solid, mp: 124°-26° C.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate (3×200 ml)
  3. washThe organic phase was washed with water and saturated calcium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of solvent in vacuo
  6. customgave an oil which
  7. customwas purified by chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-a7520fd548084caeaa1dda9e18c00fe4
Source dataset
uspto-grants-1998_05
Patent number
US05753661

Reaction notes

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