Hydrochloric Acid → 4-Hydroxy-3,5-diiodobenzoic acid 2-iodobenzyl Ester

HRID 1839911Notes

Reaction equation

HRID 1839911 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:12])[C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[I:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Cl.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[I:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][O:6][C:5](=[O:7])[C:4]1[CH:3]=[C:2]([I:1])[C:10]([OH:11])=[C:9]([I:12])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 12065Ioxynic acidHCID 1010641-(Chloromethyl)-2-iodobenzene

Product 1

HCID 99604464-Hydroxy-3,5-diiodobenzoic acid 2-iodobenzyl EsterYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3,5-diiodo-4-hydroxybenzoic acid (1 95 mg, 0.5 mmol, 2-iodo benzyl chloride (320 mg, 1.25 mmol), and cesium carbonate (490 mg, 1.5 mmol) in 5 mL DMF was stirred for 15 hours at room temperature. The mixture was then poured into 1 M HCl (100 mL) and a white precipitate formed. The precipitate was isolated filtration and was recrystallized from hot isopropanol/chloroform, yielding the title compound as bright white crystals (140 mg, 61%). 1H NMR (400 MHz, CDC13): δ 8.40 (s, 2H), 7.90 (dd, J=8.0, 1.2 Hz, 1H), 7.44-7.36 (m, 2H), 7.06 (td, J=8.0, 2.0 Hz, 1H), 6.14 (s, 1H), 5.35 (s, 2H).

Workup

  1. customa white precipitate formed
  2. customThe precipitate was isolated
  3. filtrationfiltration
  4. customwas recrystallized from hot isopropanol/chloroform

Sources & evidence

ORD record
ord-ce0c2eef04da417ba8c88b6923a70f82
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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