Iodine → 2-Iodo-5-methylbenzoic acid

HRID 515922Notes

Reaction equation

HRID 515922 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(O)(=O)C.C(O)(=O)C.[I:19]C1C=CC=CC=1.II>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCCl.C(O[Pd]OC(=O)C)(=O)C>[I:19][C:8]1[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=1[C:5]([OH:7])=[O:6]

Participants

7

Reactant 3

HCID 807IodineHCID 74183-Methylbenzoic acidHCID 12217721Iodo benzene diacetate

Product 1

HCID 1429412-Iodo-5-methylbenzoic acid

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 167845palladium(II) acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

3-Methylbenzoic acid (6.12 g; 45 mmol), iodobenzene diacetate (14.49 g; 45 mmol), tetrabutylammonium iodide (16.62 g, 45 mmol), iodine (11.43 g; 45 mmol) and diacetoxypalladium (0.5 g; 2.2 mmol) are dissolved in 1,2-dichloroethane, and then the mixture is heated in a sealed tube at 85° C. for 1 hour and 45 minutes. The cooled solution is purified by chromatography over silica gel using dichloromethane and methanol as eluants to yield the title compound.

Workup

  1. customThe cooled solution is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-c37f594a217845a8a20602dda4347c3f
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

Loading…