Isopropyl iodide → Isopropyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate

HRID 1371023Notes

Reaction equation

HRID 1371023 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[CH2:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH:20](I)([CH3:22])[CH3:21]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH:20]([O:15][C:14](=[O:16])[C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:19])=[CH:18][CH:17]=1)([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 6362Isopropyl iodideHCID 185102554-[2-(4-Fluorophenyl)-2-oxoethyl]benzoic acid

Product 1

HCID 18510263Isopropyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzoateYield 43.1%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoic acid (Example 3, Step 1) (0.600 g, 2.32 mmol) in toluene(25 ml) was added silver carbonate (1.06 g) and isopropyl iodide (0.70 g).The reaction was refluxed for 2 hour. The reaction mixture was filtered on a pad of silica gel and washed with hexane/ethyl acetate 20%. to give (0.3 g) of the title compound.

Workup

  1. temperaturewas refluxed for 2 hour
  2. filtrationThe reaction mixture was filtered on a pad of silica gel
  3. washwashed with hexane/ethyl acetate 20%

Sources & evidence

ORD record
ord-5bfb3ae45b804021868673cc96d71dae
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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