Hydrochloric Acid → 2-(4-Iodophenyl)benzoic acid

HRID 1865060Notes

Reaction equation

HRID 1865060 reaction equation
CC(C)([O-:4])C.[K+].[I:7][C:8]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[CH:9]=1.O.Cl>ClCCl.C(COC)OC>[I:7][C:8]1[CH:9]=[CH:10][C:18]([C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]([OH:21])=[O:4])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2486172-Iodo-9-fluorenoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 124128012-(4-Iodophenyl)benzoic acidYield 772%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Add potassium tert-butoxide (5.61 g, 0.05 moles) and dimethoxyethane (67 mL) to a 250 mL 3-neck round-bottom flask equipped with a magnetic stirrer, internal temperature probe, and a nitrogen inlet. Stir the mixture at ambient temperature until the solid dissolves. Add 2-iodofluoren-9-one (1.5 grams, 0.005 moles, preparation 54) and stir until the solid dissolves. Add water (0.27 grams, 0.015 moles) and stir the reaction mixture at 23° C. for 1 hour. Add dichloromethane (70 mL) and concentrated hydrochloric acid to pH 1.0. Add water (50 mL) and separate the phases. Concentrate the organic phase under reduced pressure (15-25 mm) to a solid, and suspend the solid in a mixture of hexane (5 mL) and methyl-tert-butyl ether (5 mL) at ambient temperature for 3 hours. Isolate the solid by filtration and rinse the filter cake with pentane. Vacuum dry the solids to provide the title compound (1.25 grams, 0.0386 moles, 77.1% yield). 1H NMR (acetone-d6, 500.0 MHz): δ 7.94 (dd, 1H, J=1, 7.5); 7.82 (app. d, 2H, J=8); 7.66 (td, 1H, J=1, 7.5); 7.55 (td, 1H, J=1, 8); 7.44 (dd, 1H, J=1, 7.5); 7.22 (app. d, 2H, J=8).

Workup

  1. customequipped with a magnetic stirrer
  2. dissolutiondissolves
  3. dissolutiondissolves
  4. customAdd water (50 mL) and separate the phases
  5. concentrationConcentrate the organic phase under reduced pressure (15-25 mm) to a solid
  6. additionin a mixture of hexane (5 mL) and methyl-tert-butyl ether (5 mL) at ambient temperature for 3 hours
  7. customIsolate the solid
  8. filtrationby filtration
  9. washrinse the filter cake with pentane
  10. customVacuum dry the solids

Sources & evidence

ORD record
ord-364e6f0443ad4f35847713c1e7e17f39
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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